Unprecedented Grob-type fragmentation of 5-dioxolan-bicyclo[4.2.0]octan-2-ones into 3-(methoxycarbonylmethyl)cyclohexanones

被引：13

作者：

DeGiacomo, M

Bettolo, RM

Scarpelli, R

机构：

[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO CHIM,I-00185 ROME,ITALY

[2] UNIV ROMA LA SAPIENZA,CNR,CTR STUDIO CHIM SOSTANZE ORGAN NAT,I-00185 ROME,ITALY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(97)00657-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The unprecedented Grob-type fragmentations of 5-dioxolan-bicyclo[4.2.0]octan-2-ones 1 into 3-(methoxycarbonylmethtl)cyclohexanes 2 are described. This fragmentation, in combination with the allene photoannelation used to produce compounds 1, might constitute an indirect way for achieving: conjugate addition of methyl acetate; new syntheses of kaurane, stemarane and thirsiflorane diterpenes might be also envisaged from 2c and 2d. (C) 1997 Elsevier Science Ltd.

引用

页码：3469 / 3470

页数：2

共 9 条

[1]

Bartoletti A, 1996, GAZZ CHIM ITAL, V126, P223

[2] A formal total synthesis of (+)-methyl trachyloban-18-oate and (+)-methyl 16-oxo-17-norkauran-18-oate: Regio- and diastereoselective preparation of methyl (13S)-13-hydroxyisoatisiren-18-oate from (-)-abietic acid [J].