HYPERVALENT ORGANOIODINE COMPOUNDS - RADICAL FRAGMENTATION OF OXABICYCLIC HEMIACETALS - CONVENIENT SYNTHESIS OF MEDIUM-SIZED AND SPIRO LACTONES

被引：36

作者：

ARENCIBIA, MT

FREIRE, R

PERALES, A

RODRIGUEZ, MS

SUAREZ, E ^{[1
]}

机构：

[1] CSIC,INST PROD NAT & AGROBIOL,LA LAGUNA,SPAIN

[2] INST ROSCASOLANO,DEPT CRISTALOG,E-28006 MADRID,SPAIN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期

关键词：

D O I：

10.1039/p19910003349

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of steroidal models of oxyabicyclic hemiacetals such as 2-oxabicyclo[4.4.0]decan-1-ol, 9-oxabicyclo[4.3.0]nonan-1-ol and 2-oxabicyclo[3.3.0]octan-1-ol, in the presence of (diacetoxyiodo)benzene and iodine afforded, through ring expansion, ten-, nine- and eight-membered lactones, respectively. Spiro lactones of dihydropyran-5-spirocyclohexan-2(3H)-one and dihydrofuran-4-spirocyclohexan-2(3H)-one types were obtained by photolysis of steroidal models of 2-oxabicyclo[2.2.2]octan-1-ol and 7-oxabicyclo[3.2.1]octan-1-ol, respectively.

引用

页码：3349 / 3360

页数：12

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