Total synthesis of (±)-dihydroprotolichesterinic acid and formal synthesis of (±)-roccellaric acid by radical cyclisation of an epoxide using a transition-metal radical source

被引：33

作者：

Mandal, PK ^{[1
]}

Roy, SC ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Calcutta 700032, W Bengal, India

来源：

TETRAHEDRON | 1999年 / 55卷 / 37期

关键词：

dihydroprotolichesterinic acid; roccellaric acid; radical cyclisation; epoxide; transition matal;

D O I：

10.1016/S0040-4020(99)00635-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and efficient total synthesis of (+/-)-Dihydroprotolichesterinic acid (1) and Formal synthesis of (+/-)-Roccellaric acid (2) has been acheived by radical cyclisation of epoxide using a transition metal radical source. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：11395 / 11398

页数：4

共 23 条

[1] ENANTIOSELECTIVE SYNTHESIS OF HYDROXY ALPHA-AMINO-ACIDS - (-)-ERYTHRO-GAMMA-HYDROXYNORVALINES AND (-)-THREO-GAMMA-HYDROXYNORVALINES
ARIZA, J
FONT, J
ORTUNO, RM
[J]. TETRAHEDRON, 1990, 46 (06) : 1931 - 1942
[2] ASAHINA Y, 1936, CHEM BER, V69, P120
[3] A CONCISE SYNTHESIS OF (-)-DIHYDROPROTOLICHESTERINIC ACID VIA CONSECUTIVE STEREOCONTROLLED 1,4-CONJUGATE ADDITION AND SYN-ALDOL CONDENSATION-REACTIONS
BANKS, MR
DAWSON, IM
GOSNEY, I
HODGSON, PKG
THORBURN, P
[J]. TETRAHEDRON LETTERS, 1995, 36 (20) : 3567 - 3570
[4] LACTONE ALIPHATIC ACIDS AS ANTIBACTERIAL AGENTS
CAVALLITO, CJ
FRUEHAUF, DM
BAILEY, JH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (11) : 3724 - 3726
[5] Efficient total syntheses of (±)protolichesterinic acid and (±)rocellaric acid via tungsten-π-allyl complexes
Chen, MJ
Liu, RS
[J]. TETRAHEDRON LETTERS, 1998, 39 (51) : 9465 - 9468
[6] Saturated and unsaturated lactones
Collins, I
[J]. CONTEMPORARY ORGANIC SYNTHESIS, 1997, 4 (04): : 281 - 307
[7] GRIECO PA, 1975, SYNTHESIS-STUTTGART, P67
[8] Hansch C., 1990, COMPREHENSIVE MED CH
[9] Hesse O. J., 1898, PRAKT CHEMIE, V57, P232
[10] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES
HOFFMANN, HMR
RABE, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02): : 94 - 110

← 1 2 3 →