A concise total synthesis of (+/-)-cis- and (+/-)-trans-clavicipitic acids by combinational use of directed lithiation and fluoride ion-induced elimination-addition reaction of 1-(triisopropylsilyl)gramine derivatives

被引：32

作者：

Iwao, M ^{[1
]}

Ishibashi, F ^{[1
]}

机构：

[1] NAGASAKI UNIV,FAC FISHERIES,NAGASAKI 852,JAPAN

来源：

TETRAHEDRON | 1997年 / 53卷 / 01期

关键词：

D O I：

10.1016/S0040-4020(96)00977-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A six-step total synthesis of (+/-)-clavicipitic acid (1) from 1-(triisopropylsilyl)gramine (2) was achieved by combinational use of 4-selective lithiation of 2 and fluoride ion-induced elimination-addition reaction of 4-[(E)-3-hydroxy-3-methyl-1-butenyl]-1-(triisopropylsilyl) (7) as key reactions. Separation of cis- and trans-diastereomers (1a and 1b) were easily accomplished by simple fractional crystallization and column chromatography. The overall yields of 1a and 1b from 2 were 21% and 17%, respectively. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：51 / 58

页数：8

共 24 条

[1] SYNTHESIS OF PRENYLATED QUINONES BY THE OXIDATIVE-DEGRADATION APPROACH - BIRCH VS VINYLOGOUS BIRCH HYDROGENOLYSIS (BIHY VS VIBIHY) IN CONTROLLING (2)DELTA-STEREOCHEMISTRY OF THE PRENYL CHAIN [J].