STEREOSELECTIVE TOTAL SYNTHESIS OF THE TETRACYCLIC DITERPENES HIBAOL AND DIHYDROHIBAENE

被引：32

作者：

KAMETANI, T

SUZUKI, K

NEMOTO, H

FUKUMOTO, K

机构：

[1] Pharmaceutical Institute, Tohoku University, Sendai 980, Aobayama

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 07期

关键词：

D O I：

10.1021/jo01321a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermolysis and desulfurization of 5-[(n-butylthio)methylene]-2-[2-(4-methoxybenzocyclobutenyl)ethyl]-2-methylcvclopentanone (3) and the 5-methoxybenzocyclobutenyl analogue (4) gave stereoselectively l, 2, 3, 4, 4α, 9, 10, 10a-octahydro-7-methoxy-2α-methyl-2β, 10aβ-ethanophenanthren-l-one (17) and the 6-methoxy isomer 18, potential intermediates. Intermediate 18 was stereoselectively converted into the tetracyclic diterpenoid containing a bicyclo[3.2.1]octane system hibaol (1). This also constitutes a total synthesis of dihydrohibaene (2). © 1979, American Chemical Society. All rights reserved.

引用

页码：1036 / 1043

页数：8

共 30 条

[1]

BEAMES DJ, 1969, CHEM COMMUN, P498

[2]

COOK IF, 1970, TETRAHEDRON LETT, P4091

[3] NEW METHODS FOR CARBOCYCLIC SNYTHESIS APPLICABLE TO GIBBERELLIC ACIDS - STEREOSELECTIVE INTRODUCTION OF ANGULAR VINYL GROUPING AND PINACOLIC CYCLIZATION OF KETO ALDEHYDES [J].