Facile synthesis of L-3,4-didehydrovaline constituting an antibiotic, phomopsin A

A convenient synthesis of beta,gamma-unsaturated valine (L-3,4-didehydrovaline). an important constituent of an antibiotic phomopsin A, was achieved from H-D-Ser-OH through a seven-step conversion in 31% overall yield.

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 5; pp. 634 - 636
Main Authors Yonezawa, Y, Shimizu, K, Yoon, KS, Shin, CG
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
didehydrovaline
Grignard reaction
Jones' oxidation
beta-elimination
amino acids
ESTERS
deprotection
IRREVERSIBLE ENZYME-INHIBITORS
UNSATURATED AMINO-ACIDS
BETA
DEHYDROOLIGOPEPTIDES
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More Information
Summary:A convenient synthesis of beta,gamma-unsaturated valine (L-3,4-didehydrovaline). an important constituent of an antibiotic phomopsin A, was achieved from H-D-Ser-OH through a seven-step conversion in 31% overall yield.
ISSN:0039-7881
DOI:10.1055/s-2000-6382