Enantioselective Synthesis of (+)-Polyanthellin A via Cyclopropane-Aldehyde (3+2)-Annulation

被引：17

作者：

Campbell, Matthew J. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

SYNTHESIS-STUTTGART | 2010年 / 16期

关键词：

annulation; total synthesis; heterocycles; Lewis acids; ring opening; ASYMMETRIC-SYNTHESIS; INTRAMOLECULAR CYCLOPROPANATION; ALLYLIC OXIDATION; GENERAL STRATEGY; SCLEROPHYTIN-A; DITERPENES; CLADIELLIN; METATHESIS; CATALYST; DELTA(5)-STEROIDS;

D O I：

10.1055/s-0030-1258151

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of the cladiellin diterpene natural product (+)-polyanthellin A is described. The core tetrahydrofuran was constructed using a stereospecific and stereoselective (3+2)-annulation of a donor-acceptor cyclopropane and a labile beta-silyloxy aldehyde. These particular reactants necessitated the application of a new Lewis acid, MADNTf(2) [(ArO)(2)AlNTf2], to avoid competitive elimination. Ring-closing metathesis was employed to form the oxonane ring at C3-C4 and give a functional group handle that could be elaborated to the natural product.

引用

页码：2841 / 2852

页数：12

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