A radical cyclization strategy for the concise total synthesis of (+/-)-geissoschizine

被引：43

作者：

Takayama, H

Watanabe, F

Kitajima, M

Aimi, N

机构：

[1] Faculty of Pharmaceutical Sciences, Chiba University, Chiba, 263, 1-33, Yayoi-cho, Inage-ku

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(97)01186-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthetic route to (+/-)-geissoschizine (1) was developed that features the construction of a Corynanthe-skeleton via radical cyclization of vinyl iodide, which was easily prepared by assembly of three fragments. New pentacyclic molecules formed by the radical cyclization were also reported. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：5307 / 5310

页数：4

相关论文

共 19 条

[1] A NEW SYNTHESIS OF INDOLO[2,3-ALPHA]QUINOLIZIDINE DERIVATIVES - A FORMAL TOTAL SYNTHESIS OF (+/-)-GEISSOSCHIZINE [J].

BANKS, BJ ;

CALVERLEY, MJ ;

EDWARDS, PD ;

HARLEYMASON, J .

TETRAHEDRON LETTERS, 1981, 22 (17) :1631-1634

[2] A concise, stereoselective synthesis of (+/-)-geissoschizine [J].

Bennasar, ML ;

Jimenez, JM ;

Sufi, BA ;

Bosch, J .

TETRAHEDRON LETTERS, 1996, 37 (50) :9105-9106

[3]

BOHLMANN C, 1985, LIEBIGS ANN CHEM, P1752

[4] TOTAL SYNTHESIS OF (+/-)-ALPHA- AND (+/-)-BETA-COPAENES AND YLANGENES [J].

COREY, EJ ;

WATT, DS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2303-2311

[5] REACTION OF ORGANOTIN HYDRIDES WITH ACETYLENIC ALCOHOLS [J].

ENSLEY, HE ;

BUESCHER, RR ;

LEE, K .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (03) :404-408

[6] REACTIONS WITH INDOLE-DERIVATIVES .31. STEREOSELECTIVE TOTAL SYNTHESES OF GEISSOSCHIZINE [J].

HACHMESTER, B ;

THIELKE, D ;

WINTERFELDT, E .

CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (12) :3825-3836

[7]

HERBERT RB, 1994, MONOTERPENOID IN 4 S, pCH1

[8] Short synthetic route to (+/-)-geissoschizine [J].

Lounasmaa, M ;

Jokela, R ;

Anttila, U ;

Hanhinen, P ;

Laine, C .

TETRAHEDRON, 1996, 52 (19) :6803-6810

[9] NEW, SHORT SYNTHESIS OF (+/-)-GEISSOSCHIZINE [J].

LOUNASMAA, M ;

JOKELA, R ;

MIETTINEN, J ;

HALONEN, M .

HETEROCYCLES, 1992, 34 (08) :1497-1502

[10] A CONCISE STRATEGY FOR THE SYNTHESES OF INDOLE ALKALOIDS OF THE HETEROYOHIMBOID AND CORYNANTHEIOID FAMILIES - TOTAL SYNTHESES OF (+/-)-TETRAHYDROALSTONINE, (+/-)-CATHENAMINE, AND (+/-)-GEISSOSCHIZINE [J].

MARTIN, SF ;

BENAGE, B ;

HUNTER, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5925-5927