Regular Issue

Vol. 53, No. 7, 2000

19 data found. 1 - 19 listed
Communication | Regular issue | Vol 53, No. 7, 2000, pp. 1471 - 1474
Published online:
DOI: 10.3987/COM-00-8900
Suggestion of Unexpected Sulfur Dioxide Mechanism for Deoxygenations of Pyridine N -Oxides with Alkanesulfonyl Chlorides and Triethylamine

Yoshiki Morimoto,* Hajime Kurihara, Takamasa Shoji, and Takamasa Kinoshita

*Department of Chemistry, Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan


The reaction mechanism for unusual deoxygenations of pyridine N-oxides with alkanesulfonyl chlorides and triethylamine was explored. Some experimental facts suggested that sulfur dioxide generated in the reaction system might be responsible for the deoxygenations without chlorinations of the pyridine nucleus.

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Communication | Regular issue | Vol 53, No. 7, 2000, pp. 1475 - 1478
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DOI: 10.3987/COM-00-8912
(-)-Ampelopsin D is Different from (-)-Quadrangularin A

Masatake Niwa,* Junko Ito, Kenji Terashima, Tomoko Koizumi, Yoshiaki Takaya, and Ke-Xu Yan

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan


The structure of (—)-ampelopsin D, hydroxystilbene dimer, was reinvestigated using spectroscopic methods. Furthermore, the relative and absolute stereostructures were discussed on the basis of chemical transformation of (+)-ε-viniferin to (—)-ampelopsin D.

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Communication | Regular issue | Vol 53, No. 7, 2000, pp. 1479 - 1483
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DOI: 10.3987/COM-00-8913
β-Lactam Synthesis by Diastereoselective Condensation of Chiral 3-(p-Tolylsulfinyl)-2-furaldimine and Ester Enolates

Yoshitsugu Arai,* Shinya Yoneda, Tsutomu Masuda, and Yukio Masaki

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


Highly diastereoselective condensation of chiral sulfinyl-substituted furaldimine with lithium ester enolates has been achieved, affording (3R)-syn-β-lactams and/or (3R)-syn-β-amino esters, as the major products

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Communication | Regular issue | Vol 53, No. 7, 2000, pp. 1485 - 1488
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DOI: 10.3987/COM-00-8920
Palladium-catalyzed Asymmetric Allylic Alkylation Using Chiral P,N-Ligands

Takashi Mino,* Youichi Tanaka, Masami Sakamoto, and Tsutomu Fujita

*Department of Materials Technology, Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (8) with a dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of new chiral P,N-ligands 5 in good yields with good enan-tioselectives (up to 83% ee).

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Paper | Regular issue | Vol 53, No. 7, 2000, pp. 1489 - 1498
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DOI: 10.3987/COM-00-8890
Synthesis of Indolylpyrimidines via Cross-Coupling of Indolylboronic Acid with Chloropyrimidines: Facile Synthesis of Meridianin D

Biao Jiang* and Cai-guang Yang

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China


Palladium catalyzed cross-coupling reaction of 3-indolylboronic acid with 2,4-dichloropyrimidines proceeded regioselectively to yield indolyl- or bis(indolyl)pyrimidines in high yield, depending on the projection of 3-indolylboronic acid. The marine indole alkaloid meridianin D and an analogue were synthesised via the palladium catalyzed cross-coupling reaction as a key step.

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Paper | Regular issue | Vol 53, No. 7, 2000, pp. 1499 - 1504
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DOI: 10.3987/COM-00-8902
A Concise Access to 6-Azabicyclo[3.1.0]hexanes via High-Pressure Promoted Cycloaddition Reaction of Azides to ABH

Minoru Ishikura,* Sayoko Kudo, Ayako Hino, Nobuyuki Ohnuki, and Nobuya Katagiri*

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


Cycloaddition reaction of electron-deficient azides (5a, b) to 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) (1) was accelerated by high-pressure, leading to a mixture of regioisomeric triazolines (6) in good yields. Then, 6 were in turn, through photolysis and ring opening sequences, converted to 6-azabicyclo[3.1.0]hexanes (8).

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Paper | Regular issue | Vol 53, No. 7, 2000, pp. 1505 - 1513
Published online:
DOI: 10.3987/COM-00-8907
Synthesis of (-)-Sugiresinol Dimethyl Ether Utilizing (-)-Quinic Acid

Keizo Matsuo,* Wakiko Sugimura, Yumiko Shimizu, Keiji Nishiwaki, and Hiroshi Kuwajima

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashiosaka, Osaka 577-8502, Japan


(-)-Sugiresinol dimethyl ether, a derivative of (-)-sugiresinol isolated from Cryptomeria japonica, was synthesized through 1,4-conjugate addition of arylmetal reagent to a substituted chiral 2-cyclohexen-1-one derived from (-)-quinic acid.

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Paper | Regular issue | Vol 53, No. 7, 2000, pp. 1515 - 1522
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DOI: 10.3987/COM-00-8911
Chemistry of Indoles Carrying a Basic Function. Part VI. Synthesis of a New Ring System with Indole Nucleus

István Moldvai, Mihály Balázs, Eszter Gács-Baitz, Tünde Platthy, Eszter Temesvári-Major, and Csaba Szántay*

*Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H-1525 Budpest II, Pusztaszeri ut 59-67, P.O. Box 17, Hungary


Stobbe condensed product half ester (2E;E-1,3,4,5-tetrahydrobenz[c,d]indole-5-ylidene-3’-ethoxycarbonylpropionic acid) afforded a monomer tetracyclic indole derivative (4; 5-ethoxycarbonyl-7-acetoxy-1H,9cH-3,4-dihydronaphto[c,d,e]indole) and a dimer (5; 5-ethoxycarbonyl-1H,9cH-3,4-dihydronaphto[c,d,e]indole-7-(O-E-1,3,4,5-tetrahydrobenz[c,d]indole-5-ylidene-3’-ethoxycarbonylethylpropionate) in an unexpected cyclisation.

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Paper | Regular issue | Vol 53, No. 7, 2000, pp. 1523 - 1532
Published online:
DOI: 10.3987/COM-00-8917
Solid-Phase Synthesis of 2-Phenyl-4-quinolinone Library via Flavylium Salt

Shingo Sato,* Yutaka Kubota, Hironobu Kumagai, Toshihiro Kumazawa, Shigeru Matsuba, Jun-ichi Onodera, and Masanobu Suzuki*

*Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jyonan, Yonezawa 992-8510, Japan


Fourteen 1-, 6-, 7-, 8-mono-, 7,8-di-, and 6,7,8-trisubstituted 2-(4’-hydroxy- and 4’-hydroxy-3’-methoxy)phenyl-4-quinolinones were conveniently synthesized by aqueous ammonia treatment of the flavylium salts obtained by the three-components condensation reaction of acetophenones, aldehydes, and ethyl orthoformate on a solid support with excellent purity and in overall yields of 11-59%.

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Paper | Regular issue | Vol 53, No. 7, 2000, pp. 1533 - 1549
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DOI: 10.3987/COM-00-8922
LI-F Antibiotics, a Family of Antifungal Cyclic Depsipeptides Produced by Bacillus polymyxa L-1129

Jun Kuroda, Toshio Fukai, Masataka Konishi, Jun Uno, Keiji Kurusu, and Taro Nomura*

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Twelve antifungal depsipeptide antibiotics named as LI-F03a, LI-F03b, LI-F04a, LI-F04b, LI-F05a, LI-F05b, LI-F06a, LI-F06b, LI-F07a, LI-F07b, LI-F08a and LI-F08b have been isolated from the fermentation broth of Bacillus polymyxa L-1129 by use of extensive preparative HPLC. Not only their intrinsic antifungal and anti-Gram positive bacterial activity, they also showed unique synergistic antifungal effect in combination with the azole group antifungal agents. The structural studies disclosed that they are cyclic depsipeptides composed of six amino acids (three of them, L-threonine, D-allo-threonine and D-alanine being in common among all components and other three amino acids variable) on which is substituted by a 15-guanidino-3-hydroxypentadecanoic acid.

Note | Regular issue | Vol 53, No. 7, 2000, pp. 1551 - 1557
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DOI: 10.3987/COM-00-8881
Synthesis of 2-Ethylthio-6-(3-hydroxy-1,2-O -isopropylidenepropyl)pteridin-4(3H )-one

Yonghan Kang,* Seungjin Kim, Youngchan Myoung, and Daejin Baek

*Department of Chemistry, Hanyang University, Ansan, Kyunggi-do 425-791, Korea


A strategy has been described for the synthesis of 2-ethylthio-6-(3-hydroxy-1,2-O-isopropylidenepropyl)pteridin-4(3H)-one, which can be used as a useful intermediate for the conversion of neopterin to biopterin.

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Note | Regular issue | Vol 53, No. 7, 2000, pp. 1559 - 1568
Published online:
DOI: 10.3987/COM-00-8887
Syntheses of Bis(3’-indolyl)-2(1H)-pyrazinones

Biao Jiang* and Xiao-Hui Gu

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China


The syntheses of 3,6-bis(3’-indolyl)-2(1H)-pyrazinone and 3,5-bis(3’-indolyl)-2(1H)-pyrazinone were described. Syntheses of 3,6-bis(3’-indolyl)-2(1H)-pyrazinone proceeded through the condensation of N-Boc-indolylglycine with indol-3-yl-N-methyl-O-methoxyglycinamide, and followed by reduction with LiAlH4 and cyclization of the resulting bisindolyl aldehyde-amine. 3,5-Bis(3’-indolyl)-2(1H)-pyrazinone was synthesized by cyclization of bisindolyl ketone amine in excess of ammonia under pressure.

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Note | Regular issue | Vol 53, No. 7, 2000, pp. 1569 - 1572
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DOI: 10.3987/COM-00-8894
A Synthesis of Cytonin (Taiwanin A), an Antitumor Lignan

Weir-Torn Jiaang, Chih-Liang Wang, Albert Tseng, and Shui-Tein Chen*

*Institute of Biological Chemistry, Academia Sinica, Taipei, 115, Taiwan, R.O.C.


A new procedure for the synthesis of the antitumor substance: cytonin (taiwanin A) is described. Stobbe reaction, using diethyl succinate with piperonal in a 2:1 molar ratio, produced 2E,3E-dipiperonylidenesuccinic acid. Dehydration to the anhydride, followed by reduction with DIBALH gave hydroxy acid. Subsequent cyclization of the hydroxy acid resulted in 21% total yield of cytonin.

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Note | Regular issue | Vol 53, No. 7, 2000, pp. 1573 - 1578
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DOI: 10.3987/COM-00-8908
The First and Simple Total Synthesis of Cappariloside A

Masanori Somei* and Fumio Yamada

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


A lithium hydroxide promoted simple glycosylation of 4-hydroxyindole-3-acetonitrile with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide was developed. Utilizing the method, the first and five steps total synthesis of cappariloside A was achieved from indole-3-carbaldehyde in 41% overall yield.

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Note | Regular issue | Vol 53, No. 7, 2000, pp. 1579 - 1582
Published online:
DOI: 10.3987/COM-00-8914
A Convenient Method for the Synthesis of C-10 Alkylated Docetaxel Analogs Using Tris-(trimethylsilyl)silane as a Radical Mediator

Shin Iimura, Satoru Ohsuki, Kouichi Uoto, Kiyoshi Nakayama, Hirofumi Terasawa, and Tsunehiko Soga*

*New Product Research Laboratories IV, Daiichi Pharmaceutical Co., Ltd., 1-16-13, Kitakasai, Edogawa, Tokyo 134-8630, Japan


Radical coupling has been investigated as a method for preparing Docetaxel analogs substituted at the C-10 position. C-10-Xanthate derivatives of 7-O-TES-10-deacetylbaccatin III were coupled with acrolein using organosilanes as radical mediators. Among the organosilanes that were investigated, tris(trimethylsilyl)silane gave the best results. This method provides C-10 alkylated baccatin III in good yield, and avoids the use of potentially toxic tributyltin hydride.

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Note | Regular issue | Vol 53, No. 7, 2000, pp. 1583 - 1587
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DOI: 10.3987/COM-00-8915
Selective Electrocatalytic Oxidation of Amines Mediated by Decahydroquinolinyl-N-oxyl Radical

Yoshitomo Kashiwagi,* Futoshi Kurashima, Chikara Kikuchi, Jun-ichi Anzai, and Tetsuo Osa

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan


Electrocatalytic oxidation of amines was studied using (±)-trans,cis-4-benzoyloxy-2,2,8a-trimethyldecahydroquinolinyl-N-oxyl. The reaction with amines led to direct formation of carbonyl compounds in aqueous media in adequate conversion (> 78 %), high current efficiency (> 90 %) and high selectivity (100 %). Under anhydrous conditions, primary amines were also oxidized to the corresponding nitriles in satisfactory conversion (> 76 %), high current efficiency (> 89 %) and high selectivity (> 95 %).

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Note | Regular issue | Vol 53, No. 7, 2000, pp. 1589 - 1593
Published online:
DOI: 10.3987/COM-00-8931
2,3-Dialkylchromones from Mycobiont Cultures of the Lichen Graphis scripta

Yukiko Takenaka, Takao Tanahashi,* Naotaka Nagakura, and Nobuo Hamada

*Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan


From the cultures of spore-derived mycobionts of lichen Graphis scripta, three chromones, 5-hydroxy-2,3-dimethyl-7-methoxychromone (1), 5-hydroxy-3-hydroxymethyl-2-methyl-7-methoxychromone (2), 5-hydroxy-2-hydroxymethyl-3-methyl-7-methoxychromone (3), were isolated. Compound (1) has been characterized as a natural product for the first time. The structures of two new chromones (2) and (3)were established on the basis of spectroscopic evidences. This is the first instance of isolation of 2,3-dialkylated chromones from lichen mycobionts.

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Review | Regular issue | Vol 53, No. 7, 2000, pp. 1595 - 1605
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DOI: 10.3987/REV-00-531
Cyclodextrin Host-Guest Systems Containing Azaaromatic Moieties

Wanda Sliwa* and Barbara Dondela

*Institute of Chemistry, Pedagogical University, Al. Armii Krajowej 13/15, 42-201 Czestochowa, Poland


The chemistry of cyclodextrin host-guest complexes containing azaaromatic moieties is reviewed. Systems with azaaromatic moiety appended to the host molecule and those including an azaaromatic guest are described.

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Review | Regular issue | Vol 53, No. 7, 2000, pp. 1607 - 1630
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DOI: 10.3987/REV-00-533
Ring Transformation of Pyridines and Benzo Derivatives under the Action of C-Nucleophiles

Sergey P. Gromov*

*Center of Photochemistry, Russian Academy of Sciences, 7a ul. Novatorov, Moscow, 117421, Russia


The data on ring transformations of heterocyclic systems containing a pyridine ring on treatment with C-nucleophiles are generalized and described systematically over the period of up to 1999.

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19 data found. 1 - 19 listed