Asymmetric Total Synthesis of Pyranicin

被引：41

作者：

Crimmins, Michael T. ^{[1
]}

Jacobs, Danielle L. ^{[1
]}

机构：

[1] Univ N Carolina, Kenan & Caudill Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 12期

关键词：

RING-CLOSING METATHESIS; MITOCHONDRIAL COMPLEX-I; DESS-MARTIN PERIODINANE; CANCER-CELL GROWTH; ANNONACEOUS ACETOGENINS; SECONDARY ALCOHOLS; INHIBITORY-ACTION; DNA-POLYMERASE; SELECTIVITY; OXIDATION;

D O I：

10.1021/ol900814w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.

引用

页码：2695 / 2698

页数：4

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