STEREOSELECTIVE TRANSFORMATION OF AJMALINE INTO 3 MINOR GELSEMIUM ALKALOIDS, KOUMIDINE, (19Z)-ANHYDROVOBASINEDIOL [(19Z)-TABERPSYCHINE] AND N-DEMETHOXYRANKINIDINE AND THEIR ABSOLUTE-CONFIGURATION

被引：25

作者：

KITAJIMA, M ^{[1
]}

TAKAYAMA, H ^{[1
]}

SAKAI, S ^{[1
]}

机构：

[1] CHIBA UNIV, FAC PHARMACEUT SCI, 1-33 YAYOI CHO, CHIBA 260, JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 08期

关键词：

D O I：

10.1039/p19910001773

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ajmaline was converted into new Gelsemium alkaloids, 19Z-anhydrovobasinediol [(19Z)-taberpsychine] and N-demethoxyrankinidine, via koumidine along the biomimetic sequence, and the absolute configuration of these alkaloids was determined by these transformations.

引用

页码：1773 / 1779

页数：7

共 27 条

[1] A MILD AND STEREOSPECIFIC CONVERSION OF VICINAL DIOLS INTO OLEFINS VIA 2-METHOXY-1,3-DIOXOLANE DERIVATIVES [J].

ANDO, M ;

OHHARA, H ;

TAKASE, K .

CHEMISTRY LETTERS, 1986, (06) :879-882

[2]

BARLETT MF, 1962, J AM CHEM SOC, V84, P622

[3] RAUWOLFIA ALKALOIDS .48. OXIDATIVE DEMETHYLATION + REARRANGEMENT OF SOME AJMALINE DERIVATIVES [J].

BARTLETT, MF ;

LAMBERT, BF ;

TAYLOR, WI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (04) :729-&

[4]

COREY EJ, 1976, TETRAHEDRON LETT, P3667

[5] CONVERSION OF TETRAHYDRO-BETA-CARBOLINE ALKALOIDS INTO OXINDOLES - STRUCTURE AND PARTIAL SYNTHESES OF MITRAPHYLLINE AND RHYNCOPHYLLINE [J].

FINCH, N ;

TAYLOR, WI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (07) :1318-&

[6]

JIN HL, 1982, ACTA CHIM SINICA, V40, P1129

[7]

LIN LZ, 1989, TETRAHEDRON LETT, V30, P3354

[8] GELSAMYDINE, AN INDOLE ALKALOID FROM GELSEMIUM-ELEGANS WITH 2 MONOTERPENE UNITS [J].

LIN, LZ ;

CORDELL, GA ;

NI, CZ ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3199-3202

[9] NEW HUMANTENINE-TYPE ALKALOIDS FROM GELSEMIUM-ELEGANS [J].

LIN, LZ ;

CORDELL, GA ;

NI, CZ ;

CLARDY, J .

JOURNAL OF NATURAL PRODUCTS, 1989, 52 (03) :588-594

[10]

LIN LZ, 1990, PHYTOCHEMISTRY, V29, P3013, DOI 10.1016/0031-9422(90)87125-E

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