Baker's yeast-mediated approach to (-)-cis- and (+)-trans-Aerangis lactones

被引：44

作者：

Brenna, E ^{[1
]}

Dei Negri, C ^{[1
]}

Fuganti, C ^{[1
]}

Serra, S ^{[1
]}

机构：

[1] Politecn Milan, CNR, Ctr Studio Sostanze Organ Nat, Dipartimento Chim, I-20131 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(01)00314-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first enantioselective synthesis of natural (-)-cis-Aerangis lactone (-)-1a and its (+)-trans-diastereoisomer (+)-lb is described. The key steps in the synthesis are: (i) the enantiospecific and 100% diastereoselective baker's yeast reduction of 1,4-keto acid 2, to afford enantiopure trans- cognac lactone (+)-10; (ii) the regioselective PPL-mediated hydrolysis of the primary acetate moiety of diacetate (+)-(3S,4R)-3, obtained from (+)-10. Chain elongation by one carbon atom via cyanide substitution, and inversion of the configuration of C(5) in nitrile derivative (+)-21a are also required to complete the synthetic route to (-)-1a. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1871 / 1879

页数：9

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