The asymmetric synthesis of sphingofungin F and the determination of its stereochemistry

The asymmetric synthesis of sphingofungin F has been achieved and its stereochemistry has been determined. Its structure, including the absolute configuration of the chiral centers, was found to be similar to that of sphingofungin B or myriocin. The synthesis is based on the catalytic asymmetric ald...

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Bibliographic Details
Published inSynlett no. 3; pp. 301 - 304
Main Authors Kobayashi, S, Matsumura, M, Furuta, T, Hayashi, T, Iwamoto, S
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.1997
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
asymmetric aldol reaction
SINGLE CHIRAL SOURCE
L-PROLINE
DIELS-ALDER REACTIONS
ENANTIOSELECTIVE SYNTHESIS
sphingolipid
sphingofungin
ENANTIOMERS
ALDOL REACTIONS
ISARIA-SINCLAIRII METABOLITE
catalytic asymmetric synthesis
STEREOSELECTIVE SYNTHESIS
TRIFLUOROMETHANESULFONATES
ACHIRAL LIGANDS
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Summary:The asymmetric synthesis of sphingofungin F has been achieved and its stereochemistry has been determined. Its structure, including the absolute configuration of the chiral centers, was found to be similar to that of sphingofungin B or myriocin. The synthesis is based on the catalytic asymmetric aldol reaction, and efficient enantioselective synthesis using a small amount of a chiral source as well as the effectiveness of our synthetic strategy for the sphingofungin family has been successfully demonstrated.
ISSN:0936-5214
DOI:10.1055/s-1997-783