Synthetic studies on [4+3] cycloadditions of oxyallyls. Part 11 - Facile synthesis of the tricyclic core of sarain A. 3-oxidopyridinium betaine cycloaddition approach

被引：60

作者：

Sung, MJ ^{[1
]}

Lee, HI ^{[1
]}

Chong, Y ^{[1
]}

Cha, JK ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 12期

关键词：

D O I：

10.1021/ol9911932

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new approach to a suitably functionalized tricyclic core of sarains has been developed by means of Katritzky's cycloaddition using 3-oxidopyridinium betaines. A key step was the regioselective differentiation of the two nearly identical hydroxy groups derived from oxidative cleavage of the double bond in 8 to afford 14. A stereocontrolled construction of the tricyclic core 20 of sarains containing the requisite side chain at C-3' was achieved by an intramolecular conjugate addition.

引用

页码：2017 / 2019

页数：3

共 23 条

[11]

HEATHCOCK CH, 1995, SYNLETT, P467

[12] INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF STABILIZED AZOMETHINE YLIDES TO UNACTIVATED DIPOLAROPHILES [J].