SYNTHETIC STUDIES ON GELSEDINE ALKALOIDS .1. - STEREOSELECTIVE PREPARATION OF HYPOTHETICAL BIOGENETIC INTERMEDIATES, D-NORSARPAGINE TYPE COMPOUNDS FROM AJMALINE

被引：18

作者：

TAKAYAMA, H ^{[1
]}

HORIGOME, M ^{[1
]}

AIMI, N ^{[1
]}

SAKAI, SI ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)88787-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

D-Norsarpagine type compound (4) and its C/D ring-opening derivative (22), which were corresponding to the hypothetical biogenetic intermediate for gelsedine (6), were prepared from ajmaline (3) via the deformylation (C21) and the construction of five-membered D ring having an α-ethyl group on C20 position. © 1990.

引用

页码：1287 / 1290

页数：4

共 11 条

[1] 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-&

[2]

FOSTER GH, 1967, J CHEM SOC CHEM COMM, P21

[3]

LIU ZJ, 1988, ALKALOIDS, V33, pCH2

[4] A NEW CLASS OF INDOLE ALKALOID ELEGANSAMINE CONSTRUCTED FROM A MONOTERPENOID INDOLE ALKALOID AND AN IRIDOID [J].

PONGLUX, D ;

WONGSERIPIPATANA, S ;

TAKAYAMA, H ;

OGATA, K ;

AIMI, N ;

SAKAI, S .

TETRAHEDRON LETTERS, 1988, 29 (42) :5395-5396

[5] STUDIES ON THE INDOLE ALKALOIDS OF GELSEMIUM-ELEGANS (THAILAND) - STRUCTURE ELUCIDATION AND PROPOSAL OF BIOGENETIC ROUTE [J].

PONGLUX, D ;

WONGSERIPIPATANA, S ;

SUBHADHIRASAKUL, S ;

TAKAYAMA, H ;

YOKOTA, M ;

OGATA, K ;

PHISALAPHONG, C ;

AIMI, N ;

SAKAI, S .

TETRAHEDRON, 1988, 44 (16) :5075-5094

[6] BIOMIMETIC SYNTHESIS OF KOUMINE SKELETON - PARTIAL SYNTHESIS OF 11-METHOXYKOUMINE ( GELSEMIUM-TYPE ALKALOID ) FROM 18-HYDROXYGARDNERINE [J].

SAKAI, S ;

YAMANAKA, E ;

KITAJIMA, M ;

YOKOTA, M ;

AIMI, N ;

WONGSERIPATANA, S ;

PONGLUX, D .

TETRAHEDRON LETTERS, 1986, 27 (38) :4585-4588

[7]

SAKAI S, 1987, CHEM PHARM BULL, V35, P4668

[8]

TAKAYAMA H, 1989, CHEM PHARM BULL, V37, P2256

[9] PARTIAL SYNTHESIS AND THE ABSOLUTE-CONFIGURATION OF 2 NEW GELSEMIUM ALKALOIDS, KOUMIDINE AND (19Z)-TABERPSYCHINE [J].

TAKAYAMA, H ;

KITAJIMA, M ;

WONGSERIPIPATANA, S ;

SAKAI, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1075-1076

[10] A BIOMIMETIC CONSTRUCTION OF HUMANTENINE SKELETON [J].

TAKAYAMA, H ;

MASUBUCHI, K ;

KITAJIMA, M ;

AIMI, N ;

SAKAI, S .

TETRAHEDRON, 1989, 45 (05) :1327-1336

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