APPLICATIONS OF AN ASYMMETRIC [2 + 2]-PHOTOCYCLOADDITION - TOTAL SYNTHESIS OF (-)-ECHINOSPORIN - CONSTRUCTION OF AN ADVANCED 11-DEOXYPROSTAGLANDIN INTERMEDIATE

被引：37

作者：

SMITH, AB ^{[1
]}

SULIKOWSKI, GA ^{[1
]}

SULIKOWSKI, MM ^{[1
]}

FUJIMOTO, K ^{[1
]}

机构：

[1] UNIV PENN,RES STRUCT MATTER LAB,PHILADELPHIA,PA 19104

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 07期

关键词：

D O I：

10.1021/ja00033a033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of the novel antitumor metabolite (-)-echinosporin (1) has been achieved. Asymmetric [2 + 21-photocycloaddition of dihydrofuran acetonide (+)-8 to 2-cyclopentenone (7) constituted the cornerstone of the synthetic strategy. Mitsunobu lactonization of hemiacetal acid 43 generated the tricyclic framework of 1, which embodies a strain energy of ca. 17 kcal/mol as estimated by MNDO calculations. The successful synthetic venture permitted assignment of the absolute configuration of echinosporin. Construction of the Corey 11-deoxyprostaglandin intermediate (+)-49 further demonstrated the utility of (+)-8 as a chiral building block.

引用

页码：2567 / 2576

页数：10

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