7,7-DIMETHYLTRICYCLO[3.3.0.0/2,8]OCTAN-3-ONES AS SYNTHETIC INTERMEDIATES .6. AN IMPROVED FORMAL SYNTHESIS OF (+/-)-DESCARBOXYQUADRONE VIA HIGHLY REGIOSELECTIVE CYCLOPROPANE RING-OPENING OF TRICYCLO[3.3.0.0/2,8]OCTAN-3-ONE

被引：4

作者：

IMANISHI, T

YAMASHITA, M

MATSUI, M

TANAKA, T

MIYASHITA, K

IWATA, C

机构：

[1] Faculty of Pharmaceutical Sciences, Osaka University, Osaka 565, 1–6 Yamadaoka, Suita

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 10期

关键词：

CYCLOPROPANE RING OPENING; BICYCLO[3.2.1]OCTANE; TRICYCLO[3.3.0.02.8]OCTANE; 4H-3A; 7-ETHANOBENZOFURAN; REGIOSELECTIVITY; DESCARBOXYQUADRONE; NEIGHBORING-GROUP PARTICIPATION;

D O I：

10.1248/cpb.40.2691

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The cyclopropane ring opening reaction of 7,7-dimethyl-3-oxotricyclo[3.3.0.0(2,8)]octane-5-acetic acid (5) was examined. A regioselective C(1)-C(2) bond cleavage of 5 proceeded smoothly under acidic conditions to give a bicyclo-[3.2.1]octan-3-one derivative 7 in good yield, as a result of neighboring-group participation of the carboxyl group. The lactone 7 was then successfully transformed into the 1,4-diketone 9, a useful intermediate for total synthesis of (+/-)-descarboxyquadrone (4).

引用

页码：2691 / 2693

页数：3