TOTAL SYNTHESIS OF DL-PENTALENOLACTONE

被引：82
作者：
DANISHEFSKY, S
HIRAMA, M
GOMBATZ, K
HARAYAMA, T
BERMAN, E
SCHUDA, PF
机构：
[1] Contribution from the Department of Chemistry, University of Pittsburgh, 15260, Pittsburgh, Pennsylvania
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 23期
关键词：
D O I：
10.1021/ja00517a041
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of dl-pentalenolactone has been achieved in a stereospecific way. The key features of the synthesis were (1) a Diels-Alder route to 5-acylcyclohexenones via selective deacylation of a 4,5-diacylcyclohexenone (see 30 → 31), (2) a new route to a-methylene-5-lactones via the Brederick reagent (see 4 → 64 → 65 → 66 → 66a → 5), and (3) the stereospecific introduction of an epoxymethylenelactone via an epoxyhemiacetal (see 5 → 6). © 1979, American Chemical Society. All rights reserved.
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页码：7020 / 7031
页数：12
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