Regular Issue

Vol. 24, No. 10, 1986

33 data found. 1 - 30 listed Next Last
Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2731 - 2733
Published online:
DOI: 10.3987/R-1986-10-2731
A New Cytotoxic Alkaloid Thalifalandine

Long-Ze Lin, Shu-Fang Li, Xiang He, Guo-Qiang Song, and Zhong-Liang Chen*

*Shanghai Institute of Material Medica, Chinese Academy of Science, 354 Finglin Lu, Shanghai 200032, China


The new dimeric aporphine-benzylisoquinoline alkaloid thalifalandine (1) from Thalictrum faberi has shown the marked antitumor activity in vitro. Its structure was confirmed by chemical transformation and spectral analysis.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2735 - 2738
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DOI: 10.3987/R-1986-10-2735
Anomalous Witting Reaction of Aldonic Thioamide Derivatives. A New Mode of Thiazole Ring Formation

László Somogyi,* Pál Herczegh, and Gyula Batta

*Reseaech Group of Antibiotics, Hungarian Academy of Sciences, H-4010 Debrecen, Hungary


A new mode of thiazole ring formation and an unexpected acetoxy group elimination were observed as a result of the reaction of N-acetyl-per-O-acetylhexonic thioamides (1b and 2b) with ethoxycarbonylmethylenetriphenylphosphorane affording ethyl 2-(1’,5’-diacetoxy-penta-1’,3’-Z,E-dien-1’-yl)-4-methylthiazole-5-carboxylate (6).

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2739 - 2742
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DOI: 10.3987/R-1986-10-2739
Synthesis of a Novel Class of Condensed 1,2-Thiazine-S-oxides. Cycloaddition Reaction of N-Aryl-4H-5,7a-epoxyisoindolines with N-Sulphinylaniline

Dipak Ranjan Borthakur, Dipak Prajapati, and Jagir Singh Sandhu*

*Division of Drug and Pharmaceutical Chemistry, Regional Research Laboratory, Jorhat 785 006, Assam, India


N-Sulphinylanilins (2) reacts readily with N-aryl-4H-5,7a-epoxyisoindolines (1) to give a novel class of condensed 1,2-thiazine-S-oxides (3) in good yields.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2743 - 2748
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DOI: 10.3987/R-1986-10-2743
Models for "Fat" Nucleosides and Nucleotides: Syntheses of "Fat" Xanthine (fX), "Fat" Guanine (fG), and "Fat" Hypoxanthene (fHx) Analogues of the imidazo[4,5-e][1,4]diazepine System

Ramachandra S. Hosmane,* Anila Bhan, and Michael E. Rauser

*Labratorl for Chamical Dynamics, Department of Chemistry, University of Maryland Baltimore County, Catonsville, Maryland 21228, U.S.A.


Synthetic analogues af xanthine, guanine, and hypoxanthine, possessing the skeletal structure of imidazo[4,5-e][1,4]diazepine, are reported.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2749 - 2752
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DOI: 10.3987/R-1986-10-2749
Photocycloaddition of Diethyl Acetylenedicarboxylate to 2-Phenyl-4H-1,3-benzothiazine Derivatives

Marija Sindler-Kulyk,* Alojz Dumbovic, Dunja Arzic, Biserka Metelko, and Lajosz Fodor

*Organic Chemistry Department, Faculty of Technology, University of Zagreb, Marulicev trg 20, 41000 Zagreb, Croatia


Upon irradiation in the presence of diethyl acetylenedicarboxylate 6,7-dimethoxy-2-phenyl-4H-1,3-benzothiazine gives two main products: benzonitrile (X) and 2,3-carbethoxy-4,5-dimethoxy-7-methylbenzothiophene (XI). We report herein the first photochemical reaction of a 4H-1,3-benzothiazine derivative.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2753 - 2756
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DOI: 10.3987/R-1986-10-2753
Gracinine, a New C-19 Diterpenoid Alkaloid from Delphinium gracile DC

Antonio G. González, Rafael Díaz Acosta, José A. Gavín, and Gabriel de la Fuente*

*Instituto de Productos Naturales y Agrobiologia de Canrias, C. S. I. C./ Unversidad de La Laguna, P.O. Box 195, 38206- La Laguna, Tenerife, Spain


Gracinine, a new C-19 diterpenoid alkaloid bearing a C-12 functionality, was isolated from Delphinium gracile DC, together with the known bases gadesine, dihydrogadesine and nudicaulidine. The structure of the new compound was established by means of 1H- and 13C-nmr spectroscopy.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2757 - 2769
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DOI: 10.3987/R-1986-10-2757
Theoretical Studies of Psychotropic Drugs. Questioning the Importance of Flex-angle in Drug Efficacy

Kenny Lipkowitz,* Anthony Burkett, and Jo Landwer

*Department of Chemistry, Indiana-Purdue University, PO Box 647, Indianapolis, IN 46223, U.S.A.


MNDO calculations indicate that hetero-substituted 9,10-dihydroanthracenes are inherently planar molecules. Ring puckering is a very low energy process that can arise from intramolecular effects, e.g. peri-and/or transannular interactions as well as from intermolecular interactions like crystal packing forces. It is concluded that the angle of flexure, determined crystallographically and used as a descriptor of drug activity in several important CNS drugs, should be used with caution or not be used at all.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2771 - 2775
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DOI: 10.3987/R-1986-10-2771
Reaction of 2-Bromo-2,3-dihydro-1H-pyrazolo[1,2-a]indazolium Bromides with Alkaline Solution

Yasuo Fujimura,* Yoshiharu Nawata, and Masatomo Hamana

*Central Research Laboratories, Chugai Pharmaceutical Company, Ltd., Takada 3-41-8, Toshima-ku, Tokyo 171, Japan


Treatment of 2-bromo-2,3-dihydro-1H-pyrazolo[1,2-a]indazolium bromides (1a-c) with alkaline solution initially affords 9H-pyrazolo[1,2-a]indazolium bromides (2a-c), which are further convertible by dehydrobromination into pyrazolo[1,2-a]indazoles (3a-c). The 9-position of 3 is susceptible to attack by oxygen and acetyl cation.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2777 - 2779
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DOI: 10.3987/R-1986-10-2777
Junosmarin, a New Khellactone Ester from Citrus junos Tanaka

Motoharu Ju-ichi,* Mami Inoue, Rika Tsuda, Naomi Shibukawa, and Hiroshi Furukawa

*Faculty of Pharmaceutical Science, Mukogawa-Women‘s University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan


A new (-)-trans-khellactone ester, junosmarin, was isolated from the root bark of Citrus junos (Rutaceae) and the structure was assigned as 1 on the basis of spectral data and synthesis of its acetate 5.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2781 - 2784
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DOI: 10.3987/R-1986-10-2781
Two New Spirobenzylisoquinoline Alkaloids from Ripicapnos afrivana (Lam.) Pomel

Luis Castedo,* Domingo Domínguez, José Manuel Novo, Amelia Peralta, José Manuel Saá, and Rafael Suau

*Facultad de Química y Sección de Alcaloides, Deparamento de Química Orgánica, C. S. I. C., Santiago de Compostela, Spain


Two new spirobenzylisoquinolines, (+)-isoparfumine and (+)-africanine, have been isolated from Rupicapnos africana (Lam.) Pomel and identified spectroscopically.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2785 - 2789
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DOI: 10.3987/R-1986-10-2785
Tandem Reductive Amination and Michael Addition. Synthesis of Optically Active Pyrrolidine Nucleus

Seiki Saito, Shingo Matsumoto, Shuji Sato, Masami Inaba, and Toshio Moriwake*

*Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


Reductive amination of ethyl (E)-(4S)-4-methoxymethoxy-6-oxo-2-hexenoate, derived from (S)-malic acid, with glycine ethyl ester was relayed intramolecularly by Michael-type addition, which has led, in one pot, to N-substituted (2R,3S)-2-ethoxycarbonylmethyl-3-hydroxypyrrolidine skeleton, a promising precursor for optically active necine bases such as (+)-heliotridine.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2791 - 2792
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DOI: 10.3987/R-1986-10-2791
Methyl Group at 1-Position of Stabilized Indoles as a Protective Group

Shin-ichi Nakatsuka,* Osamu Asano, and Toshio Goto

*Laboratory of Organic Chemistry, Faculty of Agricultures, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


Methyl group at 1-position of indoie derivative 2 was removed by oxidation with benzoyl peroxide and subsequent hydrolysis.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2793 - 2796
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DOI: 10.3987/R-1986-10-2793
A Novel 1,2-Alkyl Migration of Trialkyl(4-pyrodyl)borates

Minoru Ishikura, Tsukasa Ohta, and Masanao Terashima*

*Faculty of Pharmaceutical Scicences, Higashinihonngakuen University, 1757 Kanazawa, Toubetu-cho, Ishikari-gun, Hokkaodo 061-0212, Japan


The reaction of lithium trialkyl(4-pyridyl)borates with Lewis acids or acylating agents produced 4-alkylpyridines via 1,2-alkyl migration from boron to pyridine ring.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2797 - 2802
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DOI: 10.3987/R-1986-10-2797
Novel Approach to 1H-Benzo[f]pyrrolo[1,2-a]indole-5,10-diones

Eric O. M. Orlemans, Willem Verboom, and David N. Reinhoudt*

*Laboratory of Organic Chemistry, Twente University of Technology, Enschede, The Netherlands


The Friedel-Crafts reaction product of 1,4-dimethoxynaphthalene (3) and (S)-1-(trifluoroacetyl)-2-pyrrolidinecarbonyl chloride (4) could be converted in two steps into the benzo[f]pyrrolo[1,2-a]indole 10 following two different pathways. Compound 10 could easily be dehydrated using acid to 11. Upon reduction of 10 to the corresponding hydroquinone 12, spontaneous dehydration occurred.

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Communication | Regular issue | Vol 24, No. 10, 1986, pp. 2803 - 2807
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DOI: 10.3987/R-1986-10-2803
Thermal Reactions of o-Aminophenols and Dimethyl Actylenedicarboxylate

Norio Kawahara,* Takako Shimamori, Tsuneo Itoh, and Haruo Ogura

*Hokkaido College of Pharmacy, 7-1 Katsuraoka-cho, Otaru 047-02, Japan


o-Aminophenols reacted with dimethyl acetylenedicarboxylate (DMAD) in refluxing dioxane to give 1,4-benzoxazine derivatives and their isomers. Further, novel tricyclic compounds and benzoxazole derivative were prepared in this reaction.

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Report | Regular issue | Vol 24, No. 10, 1986, pp. 2809 - 2812
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DOI: 10.3987/R-1986-10-2809
Interaction of 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) with Alcoholic Solvents

Héctor R. Bravo and Hermann M. Niemeyer*

*Departamento de Química, Facultad de Ciencias, Unversidad de Chile, Casilla 653, Santiago, Chile


Solubilities and IR spectra of DIMBOA in alcoholic solvents showed that the carbonyl group of DIMBOA is hydrogen-bonded to the solvent. Activation parameters of DIMBOA in the same solvents suggested that the decomposition of DIMBOA occurs through an isocyanate, in analogy with the reaction in aqueous and aprotic solvents.

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Report | Regular issue | Vol 24, No. 10, 1986, pp. 2813 - 2815
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DOI: 10.3987/R-1986-10-2813
The Formation and Facile Conversion of Trityl Phenylcynomethane Nitronate

Joseph H. Boyer* and Thanikavelu Manimaran

*Department of Chemistry, University of New Orleans, New Orleans, LA 70148, U.S.A.


Trityl chloride and silver phenylcyanomethane nitronate in toluene at -20°C gave trityl phenylcyanomethane nitronate 1, an unstable ester that rearranged and fragmented at 5-10°C to 1-triphenylmethoxy-4,5-diphenyl-1,2,3-triazole 6 with coproducts carbon dioxide, α,α’-bis(triphenylmethaneazo)stilbene 3, benzonitrile-N-oxide 4, and trityl isocyanate 5.

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Report | Regular issue | Vol 24, No. 10, 1986, pp. 2817 - 2820
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DOI: 10.3987/R-1986-10-2817
Syntheses of Vinylogous 4H-Pyrones from 2,6-Dimethyl-4H-pyran-4-thione and Arenyl Bromomethyl Ketones

Katsuo Ohkata, Masao Imagawa, and Kin-ya Akiba*

*Department of Chemistry, Faculty of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan


2,6-Dimethyl-4H-pyran-4-ylideneacetophenones (5) were prepared by desulfurization of mercaptopyriliurn salts (4) with diazabicyclo[5.4.0]undecene (DBU) in moderate yield. The 1H NMR spectra in CDCl3 solution of 5 show the exclusive preference for s-cis conformation at the enone site.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2821 - 2826
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DOI: 10.3987/R-1986-10-2821
Synthesis of New Cyclophosphazenes Containing Polyoxuethylene Moieties

Luciana Corda, Carlo Anchisi, Gianni Podda,* Pietro Traldi, and Mario Gleria

*Istituto di Chimica Farmaceutica, Tossicologica ed Applicate, University of Cagliari, Via Ospedale 72, 09100 Cagliari, Italy


Hexa-substituted cyclophosphazenes are formed by the reaction of hexachlorocyclophosphazenes with polyethylene glycols mono alkyl ether and employed as transfer catalysts in anion-promoted reactions.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2827 - 2830
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DOI: 10.3987/R-1986-10-2827
Dual Substituent Parameter Treatment of 13C Substituent Chemical Shifts in 5-Substitued 2-Thenylidenemalononitriles and Molecular Orbital Theoretical Analysis at the CNDO/2 Level

Sumana Datta, Asish De, Sankar Prasad Bhattacharyya,* Chitrani Medhi, and Ajit Kumar Chakraborty

*Theory Group, Department of Physical Chemistry, Indian Asociation for the Cultivation of Science, Jadavpur, Calcutta 700 032, India


DSP treatment of 13C SCS among the members of the title compound indicated the dominance of the resonance effect at Cβ and the presence of both localized and extended polarization in the side chain. MO calculations at the CNDO/2 level corroborated the observed SCS trends.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2831 - 2834
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DOI: 10.3987/R-1986-10-2831
Synthesis of Novel N-Heteroatomic Cannabinol Analogues

Marie-Claude Bellassoud-Fargeau, Bernadette Graffe, Marie-Claude Sacquet, and Pierre Maitte*

*associé au CNRS, 4 Place Jussieu, Laboratoire de Chimie des Hétérocycles, Université P. et M. Curie, case courrier 43, 4 Place Jussieu, F-75252 Paris Cedex 05, France


Cyclization of 2,2-dimethyl-3-pyrrolidinomethylene-5-hydroxy-7-pentyl-4-chromanone 2 with guanidine, formamidine, acetamidine and benzamidine hydrochlorides in the presence of 2 eq. of sodium ethoxide afforded novel 5H-[1]benzopyrano[4,3-d]pyrimidines 4a-d in good yields.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2835 - 2840
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DOI: 10.3987/R-1986-10-2835
New Syntheses of 1-Amino- and 1-(2-Aminoethyl)-2,6-dicyanopiperidines and Diazabicyclo Compounds by a Strecker Reaction Using Glutaraldehyde and Diamines, and Their Stereochemistry

Kazumasa Takahashi,* Akira Tachiki, Katsuyuki Ogura, and Hirotada Iida

*Deparment of Synthetic Chemistry, Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


An efficient sequence proposed here involves a simple Strecker reaction of glutaraldehyde with hydrazine or 1,2-diaminoethane, which gives 1-amino- or 1-(2-aminoethyl)-2,6-dicyanopiperidines, 2-cyano-1,7-diazabicyclo[4.3.0]nonane, and 10-cyano-1,4-diazabicyclo[4.4.0]decan-5-one. Their stereochemistry is also elucidated. Moreover, treatment of l-amino-2,6-dicyanopiperidine and phthaloyl dichloride in the presence of 4-(N,N-dimethylamino)pyridine quantitatively gives 1-phthalimido-2,6-dicyanopiperidine.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2841 - 2844
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DOI: 10.3987/R-1986-10-2841
Andrachamine a New Alkaloid from Andrachne aspera

Viqar Uddin Ahmad* and M. Ajmal Nasir

*H. E. J. Postgraduate Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan


A new piperidine alkaloid andrachamine was isolated from the medicinal plant Andrachne aspera. Its structure was established by spectroscopic studies.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2845 - 2855
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DOI: 10.3987/R-1986-10-2845
Synthesis of 3,6-Disubstituted β-Carbolines Which Possess either Benzodiazepine Antagonist or Agonist Activity

Timothy J. Hagen, Filadelfo Guzman, Christopher Schultz, James M. Cook,* Phil Skolnick, and Harlan E. Shannon

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.


A series of 3-substituted and 3,6-disubstituted β-carbolines have been synthesized. These compounds have been screened in vitro in order to determine the size of substituents which benzodiazepine receptors will tolerate at positions -3 and -6 of the β-carboline nucleus. It has been found that the receptor will tolerate ester alkyl groups at position-3 as large as cyclohexyl 1g but not as large as adamantyl 5d. Moreover, N-aryl substituents as large as naphthobenzylamino 8b can be introduced at position-6 without significant loss of receptor binding affinity.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2857 - 2862
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DOI: 10.3987/R-1986-10-2857
Synthesis of 2H-Pyrazolo[3,4-b]pyridines from 1,1,2,2-Tetracyanocyclopropanes

Masahiko Takahashi,* Toshiaki Orihara, Takanori Sasaki, Tetsuya Yamatera, Ken‘ichi Yamazaki, and Atomi Yoshida

*Department of Materials Sciences, Faculty of Engineering, Ibaraki University, 4-12-1 Nakanarusawamachi, Hitachi, Ibaraki 316-8511, Japan


Reaction of 3-substituted 1,1,2,2-tetracyanocyclopropanes (1) with phenylhydrazine proceeded through the formation of pyrazole-4-spirocyclopropanes (4) followed by the ring opening of the cyclopropane ring to give 4-vinylpyrazoles (5), from which 2H-pyrazolo[3,4-b]pyridines (6) were obtained.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2863 - 2870
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DOI: 10.3987/R-1986-10-2863
Preparation of Chloro-α-truxillic Acids via 3-Methyl-4-nitro-5-styrylisoxazole Photodimers

Antonella Baracchi, Stefano Chimichi, Francesco De Sio, Donato Donati, Rodolfo Nesi, Piero Sarti-Fantoni,* and Tomas Torroba

*CNR, Centro di Studio Sulla Chimica e la Struttura dei Composti Eterociclici e lolo Applicazioni, c/o Dipartimento di Chimica Organica "Ugo Schiff", Università di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy


Chloro-α-truxillic acids (3b-e) were prepared by oxidation of the photodimers (2b-e) of 3-methyl-4-nitro-5-chlorostyrylisoxazoles (1b-e).

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2871 - 2877
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DOI: 10.3987/R-1986-10-2871
Synthesis of 4,5-Dihydro-1H-imidazoles from 1,5-Dihydro-2H-imidazoles Using ‘Nickel Boride’

Melvin R. Euerby, Amanda C. Oldroyd, and Roger D. Waigh*

*Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, U.K.


In situ prepared ‘nickel boride’ generated from sodium borohydride and nickel (II) chloride cleanly transforms 1,5-dihydro-2H-imidazoles into 4,5-dihydro-1H-imidazoles in high yields by a double bond migration.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2879 - 2885
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DOI: 10.3987/R-1986-10-2879
The Preparation and Spectral Characterization of 2-Haloindoles, 3-Haloindoles, and 2,3-Dihaloindoles

Mary R. Brennan, Karen L. Erickson,* Frank S. Szmalc, Marilyn J. Tansey, and Janice M. Thornton

*Jeppson Laboratory, Clark University, Worcester, MA 01610, U.S.A.


The preparation and properties of a series of 2- and 3-haloindoles and 2,3-dihaloindoles are described, and the mechanism of halogenation of 3-halo substituted indoles is briefly discussed.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2887 - 2900
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DOI: 10.3987/R-1986-10-2887
Synthesis and Phermacodynamic Investigation of New Isoguvacine Analogues with Benzoquinolizine Skeleton

Gábor Blaskó, Julianna Kardos, Eszter Baits-Gács, Miklós Simonyi, and Csaba Szántay*

*Central Research Institute for Chemistry, Hungarian Academy of Sciences, H-1025 Budapest, Pusztaszeri ut 59-67, P.O.Box 17, Hungary


Stereoisomer hydroxy-esters 15 -19 as well as isoguvacine analogue 20 with benzo[a]quinolizine skeleton have been prepared via regioselective Dieckmann condensation of diester 9 followed by subsequent reduction and E2-elimination. Compounds 16 and 20 have shown a considerable in vitro activity at the GABA/benzodiazepine receptor complex.

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Paper | Regular issue | Vol 24, No. 10, 1986, pp. 2901 - 2904
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DOI: 10.3987/R-1986-10-2901
The Synthesis of 2,3’:2’,3"-, 2,3’:4’,3"-, 2,3’:5’,3"- and 2,2’:4’,3"-Terthienyls

Nimal Jayasuriya and Jacques Kagan*

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor St., Chicago, IL 60607-7061, U.S.A.


The coupling of thienyl Grignard reagents with the appropriate bromobithiophenes in the presence of Ni(dppp)Cl2 gave the title compounds with yields ranging between 72 and 95%.

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33 data found. 1 - 30 listed Next Last