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

共 9 条

[1] 7,7-DIMETHYLTRICYCLO[3.3.0.0/2,8]OCTAN-3-ONES AS SYNTHETIC INTERMEDIATES .1. PREPARATION AND CYCLOPROPANE RING-OPENING OF 7,7-DIMETHYL-5-(2-PROPENYL) TRICYCLO[3.3.0.0/2,8]OCTAN-3-ONE
IMANISHI, T
YAMASHITA, M
MATSUI, M
NINBARI, F
TANAKA, T
IWATA, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 1988, 36 (04) : 1351 - 1357
[2] 7,7-DIMETHYLTRICYCLO[3.3.0.0/2,8]OCTAN-3-ONES AS SYNTHETIC INTERMEDIATES .5. AN IMPROVED SYNTHESIS OF (+/-)-PENTALENENE
IMANISHI, T
YAMASHITA, M
HIROKAWA, Y
TANAKA, T
IWATA, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (05) : 1124 - 1128
[3] 7,7-DIMETHYLTRICYCLO[3.3.0.02,8]OCTAN-3-ONES AS SYNTHETIC INTERMEDIATES .4. A FURTHER EXAMINATION OF CYCLOPROPANE RING-OPENING IN THE TRICYCLO[3.3.0.02,8]OCTAN-3-ONE SYSTEM
IMANISHI, T
YAMASHITA, M
MATSUI, M
TANAKA, T
IWATA, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (11) : 3114 - 3116
[4] ANOMALOUS TRANSFORMATION OF TRICYCLO[3.3.0.0/2,8]OCTAN-3-ONES INTO BICYCLO[3.2.1]OCTAN-3-ONES, A NOVEL ROUTE TO (+/-)-QUADRONE
IMANISHI, T
MATSUI, M
YAMASHITA, M
IWATA, C
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (23) : 1802 - 1804
[5] 7,7-DIMETHYLTRICYCLO[3.3.0.02,8]OCTAN-3-ONES AS SYNTHETIC INTERMEDIATES .3. TOTAL SYNTHESIS OF (+/-)-DESCARBOXYQUADRONE
IMANISHI, T
YAMASHITA, M
MATSUI, M
TANAKA, T
IWATA, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 1988, 36 (06) : 2012 - 2016
[6] 7,7-DIMETHYLTRICYCLO[3.3.0.02,8]OCTAN-3-ONES AS SYNTHETIC INTERMEDIATES .2. A TOTAL SYNTHESIS OF (+/-)-PENTALENENE, AN ANGULAR TRIQUINANE SESQUITERPENE
IMANISHI, T
YAMASHITA, M
NINBARI, F
TANAKA, T
IWATA, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 1988, 36 (04) : 1371 - 1378
[7] Cyclopropane ring-opening of tricyclo[3.3.0.02,8]octan-3-ones: a quick access to bicyclo[3.2.1]octanones from 2-methoxyphenols
Chang, Chun-Ping
Chen, Ching-Hsien
Chuang, Gary Jing
Liao, Chun-Chen
TETRAHEDRON LETTERS, 2009, 50 (26) : 3414 - 3417
[8] ENZYMES IN ORGANIC-SYNTHESIS .8. SYNTHESIS OF ENANTIOMERICALLY PURE PROSTAGLANDIN INTERMEDIATES BY ENZYMATIC TRANSESTERIFICATION OF (1S-STAR, 5R-STAR, 6R-STAR, 7R-STAR)-(+/-)-7-HYDROXY-6-HYDROXYMETHYL-2-OXABICYCLO[3.3.0]OCTAN-3-ONE
WEIDNER, J
THEIL, F
KUNATH, A
SCHICK, H
LIEBIGS ANNALEN DER CHEMIE, 1991, (12): : 1301 - 1303
[9] ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .7. ACID-CATALYZED REARRANGEMENT OF 3-AZA-8-OXATRICYCLO[3.2.1.0/2,4]OCTAN-6-ONE ACETALS - HIGHLY STEREOSELECTIVE TOTAL SYNTHESIS OF 3-AMINO-3-DEOXY-D-ALTROSE AND DERIVATIVES
NATIVI, C
REYMOND, JL
VOGEL, P
HELVETICA CHIMICA ACTA, 1989, 72 (05) : 882 - 891

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