Toward the development of a general chiral auxiliary. A total synthesis of (+)-tetronolide via a tandem ketene-trapping [4+2] cycloaddition strategy

被引：45

作者：

Boeckman, Robert K., Jr. ^{[1
]}

Shao, Pengcheng ^{[1
]}

Wrobleski, Stephen T. ^{[1
]}

Boehmler, Debra J. ^{[1
]}

Heintzelman, Geoffrey R. ^{[1
]}

Barbosa, Antonio. J. ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 32期

关键词：

D O I：

10.1021/ja0581346

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly convergent, enantioselective total synthesis of the aglycone of the tetrocarcins, (+)-tetronolide, is described. The synthesis highlights the use of several new methods, including camphor auxiliary-directed asymmetric alkylation and the enantioselective preparation of acyclic mixed acetals bearing chirality at the acetal center, and the highly efficient connection of the two major precursors via a ketene-trapping/ intramolecular [ 4 + 2] cycloaddition strategy.

引用

页码：10572 / 10588

页数：17

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