Regular Issue

Vol. 9, No. 8, 1978

11 data found. 1 - 11 listed
Communication | Regular issue | Vol 9, No. 8, 1978, pp. 995 - 1002
Published online:
DOI: 10.3987/R-1978-08-0995
Gilletine, a New Bisbenzylisoquinoline Alkaloid from Triclisia gilletii

Daniel Dwuma-Badu, John S. K. Ayim, Albert N. Tackie, Philip D. Owusu, Joseph E. Knapp, David J. Slatkin, and Paul L. Schiff, Jr.*

*Department of Pharmaceutal Science, School of Pharmacy, University of Pittsburgh, Pittsburgh, PA 15261, U.S.A.


Gilletine (1), a new alkaloid from extracts of the leaves of Triclisia gilletii (Menispermaceae), was characterized as a dibenzodioxin bisbenzylisoquinoline base by physicochemical data and conversion to O,O-dimethylcocsulinine (3).

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Communication | Regular issue | Vol 9, No. 8, 1978, pp. 1003 - 1008
Published online:
DOI: 10.3987/R-1978-08-1003
The Reaction of Benzylideneacetone with Ethylenediamine. Evidence for the Production of Two Isomeric 1,4,8,11-Tetra-azacyclotetradeca-4,11-dienes

Peter W. R. Caulkett, David Greatbanks, Ralph W. Turner,* and John A. J. Jarvis

*Department of Chemistry, ICI Pharmaceuticals, Mereside, Alderley Park, Macclesfield, Cheshire, SK10 4TG, U.K.


The reduction of the 1,4,8,11-tetra-azacyclo-tetradeca-4,11-diene product from benzylidene acetone and ethylenediamine to give two isomeric 1,4,8,11-tetra-azacyclotetradecanes is reported. X-ray data for the condensation product of the minor isomer and glyoxal is described. The assignment of the transoid structure, (9) to the minor isomer suggests that the initial tetra-azacyclotetradeca-4,11-diene is a mixture of the diastereoisomers (2) and (3).

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Communication | Regular issue | Vol 9, No. 8, 1978, pp. 1009 - 1013
Published online:
DOI: 10.3987/R-1978-08-1009
Cimiciphytine and Norcimiciphytine — New Bisindole Alkaloids from Haplophyton cimicidum (Apocyanaceae)

M. V. Laksmikantham, Michael J. Mitchell, and Michael P. Cava*

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.


Cimiciphytine and norcimiciphytine, two new lactonic indole alkaloids isolated from Haplophvton cimicidum, have been assigned the aspidosperma-canthinone bisindole structures 3 and 4, respectively.

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Communication | Regular issue | Vol 9, No. 8, 1978, pp. 1015 - 1022
Published online:
DOI: 10.3987/R-1978-08-1015
Studies on the Synthesis of Bisindole Alkaloids. XIV. Enzyme Catalysed Formation of Leurosine

Kenneth L. Stuart, James P. Kutney,* and Brian R. Worth

*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5, Canada


Enzyme catalysed oxidation of 3’,4’-dehydrovinblastine using either horseradish peroxidase or cell free extracts from Catharanthus roseus plants provided leurosine, suggesting that the latter is in fact a natural product.

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Communication | Regular issue | Vol 9, No. 8, 1978, pp. 1023 - 1029
Published online:
DOI: 10.3987/R-1978-08-1023
Photocyclization of Heterocyclic Acylanilides

Ichiya Ninomiya,* Toshiko Kiguchi, and Takeaki Naito

*Kobe Women‘s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan


N-α,β-Unsaturated acylanilides, which contain various heterocyclic rings in their acyl groups, i.e., α-pyrone, α-fnranone, α- and β-furans, and an ortho-substituent on the benzene ring, were found to undergo photocyclization to afford various products depending upon a heterocycle, and an ortho-substituent which brought about smooth photocyclization.

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Communication | Regular issue | Vol 9, No. 8, 1978, pp. 1031 - 1040
Published online:
DOI: 10.3987/R-1978-08-1031
Cyclization Reaction of N-Substituted Mandelhydrazide with Formaldehyde

Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, Nagatoshi Wagatsuma, Toshitaka Kohagisawa, and Hitoshi Inoue

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Acid-catalysed cyclisation of N-substituted mandelhydrazides II and X with paraformaldehyde gave hexahydro-1,2,4,5-tetrazine derivatives. Furthermore, the acetyl group on the nitrogen rearranged to alcoholic oxygen during the reaction of X to give VI.

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Report | Regular issue | Vol 9, No. 8, 1978, pp. 1041 - 1046
Published online:
DOI: 10.3987/R-1978-08-1041
Molecular Structure of Azines of 3-Acetyl-4-hydroxy-2-methoxy-4-phenylcrotonic Acid Lactones

Takushi Kurihara,* Yasuhiko Sakamoto, Masanobu Mori, and Toshimasa Sasaki

*Faculty of Pharmaceutical Science, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan


Reaction of 3-acetyl-4-hydroxy-2-methoxy-4-phenylcrotonic acid lactones (2a,b) with hydrazine dihydrochloride (3) gave a mixture of azines (5a,b and 6a,b), and these structures were definitely determined by crystallographic analyses of 5b and 6b.

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Report | Regular issue | Vol 9, No. 8, 1978, pp. 1047 - 1050
Published online:
DOI: 10.3987/R-1978-08-1047
Synthesis of Methyl (R,S)-Lichensterinate

Seppo I. Pennanen*

*Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100,FIN-02015 HUT, Espoo, Finland


The methyl ester of (R,S)-lichensterinic acid was synthesized from methyl α-ketopalmitate and 1-diethylaminopropyne in three steps in 58% overall yield.

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Report | Regular issue | Vol 9, No. 8, 1978, pp. 1051 - 1057
Published online:
DOI: 10.3987/R-1978-08-1051
A Novel (E)-2-Oxoindolin-3-ylideneacxetone Dimer

Akinori Kubo,* Tatsuya Nakai, Toshikazu Nozoye, Akiko Itai, and Yoichi IItaka

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


The dimerization reaction of (E)-2-oxoindolin-3-ylideneacetone (1) is described. The structure and stereochemistry of a novel dimeric product (4) were determined by PMR, CMR analyses and confirmed by X-ray analysis.

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Review | Regular issue | Vol 9, No. 8, 1978, pp. 1059 - 1087
Published online:
DOI: 10.3987/R-1978-08-1059
Pyrroloquinolines III. Pyrrolo[3,4-b]quinolines

Misbahul Ain Khan* and João Ferreira da Rocha

*Seção de Quimica, Instituto Militar de Engenharia, Urca, 20.000 Rio de Janeiro, RJ, Brazil


In the present review various routes for the synthesis of the pyrrolo[3,4-b]quinoline system, its reactions, and the spectral data for some of the derivatives of this system are presented.

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Review | Regular issue | Vol 9, No. 8, 1978, pp. 1089 - 1119
Published online:
DOI: 10.3987/R-1978-08-1089
The Spiroindolenine Intermediate, a Review

Frank Ungemach and James M. Cook*

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


The Pictet-Spengler reaction has been employed to prepare 1,2,3,4-tetrahydro-β-carbolines for many years and is presumed to go through the spiroindolenine intermediate (XIX). A review of the evidence for this mechanism is presented.

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11 data found. 1 - 11 listed