Stereoselective synthesis of the hydrophobic side chain of scyphostatin

The hydrophobic side chain of scyphostatin was synthesized by a convergent synthetic pathway. The key reactions were the enzymatic asymmetric acetylation of a meso-diol, construction of the C12'-C13' trisubstituted E-olefin moiety by Negishi coupling, and construction of the (2' E, 4&...

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Bibliographic Details
Published inAustralian journal of chemistry Vol. 57; no. 5; pp. 439 - 447
Main Authors Takagi, R, Tsuyumine, S, Nishitani, H, Miyanaga, W, Ohkata, K
Format Journal Article
LanguageEnglish
Published CLAYTON Csiro Publishing 01.01.2004
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ROUTE
ASYMMETRIC-SYNTHESIS
PRECURSOR
HIPPOSPONGIC ACID
ANALOGS
CONFIGURATION
PI-FACIAL SELECTIVITY
CONVERGENT
NEUTRAL SPHINGOMYELINASE INHIBITOR
DISCOMYCETE
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Summary:The hydrophobic side chain of scyphostatin was synthesized by a convergent synthetic pathway. The key reactions were the enzymatic asymmetric acetylation of a meso-diol, construction of the C12'-C13' trisubstituted E-olefin moiety by Negishi coupling, and construction of the (2' E, 4' E, 6' E)-triene moiety by Horner-Wadsworth-Emmons olefination.
ISSN:0004-9425
1445-0038
DOI:10.1071/CH03298