Fusicoccin ring system by [4+4] cycloaddition. 2. A model study

被引：11
|
作者：
Sieburth, SM [1 ]
McGee, KF [1 ]
Al-Tel, TH [1 ]
机构：
[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 21期
基金：
美国国家卫生研究院;
关键词：
cycloaddition; natural products; photochemistry; pyridones;
D O I：
10.1016/S0040-4039(99)00671-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic approach to fusicoccin A utilizing intramolecular photocycloaddition of tethered 2-pyridones has been completed. This study has led to the first solvent-dependent 2-pyridone photocycloaddition yielding either cis or trans products. Epoxidation of the cis photoproduct is selective for the disubstituted alkene, stabilizes the product, and is properly located for installation of the trans-1,2-diol. Activation of the secondary amide by reaction with an isocyanate led to the reduction of the neopentyl amide carbonyl to a methyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4007 / 4010
页数：4
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