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
收藏
页码：4696 / 4710
页数：15
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