Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9-epi-Stagonolide C Employing Chiral Hexane-1,2,3,5-tetraol Derivatives as Building Blocks

被引：7

作者：

Show, Krishanu ^{[1
]}

Kumar, Pradeep ^{[1
]}

机构：

[1] CSIR Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 27期

关键词：

Asymmetric synthesis; Aldol reactions; Metathesis; alpha-Aminoxylation; STEREOSELECTIVE TOTAL-SYNTHESIS; WADSWORTH-EMMONS OLEFINATION; ASYMMETRIC ALDOL REACTIONS; EFFICIENT TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; ALPHA-AMINOXYLATION; POOL SYNTHESIS; ALDEHYDES; ALCOHOLS; SULFONYLATION;

D O I：

10.1002/ejoc.201600625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An organocatalytic approach to the synthesis of (2R,3S)-hexane-1,2,3,5-tetraol (11) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates 11 were prepared with complete stereocontrol through the proline-catalyzed intermolecular aldol reaction between acetone and d-glyceraldehyde acetonide. The synthetic utility of the intermediates was demonstrated by their transformation into the title hydroxylated pyrans and a variety of unsaturated lactones through standard synthetic protocols.

引用

页码：4696 / 4710

页数：15

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