FIRST SYNTHESIS OF BOTH ENANTIOMERS OF THE BIOTIN VITAMER 8-AMINO-7-OXOPELARGONIC ACID

Authors
LUCET D LEGALL T MIOSKOWSKI C PLOUX O MARQUET A
Citation
D. Lucet et al., FIRST SYNTHESIS OF BOTH ENANTIOMERS OF THE BIOTIN VITAMER 8-AMINO-7-OXOPELARGONIC ACID, Tetrahedron : asymmetry, 7(4), 1996, pp. 985-988
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
4
Year of publication
1996
Pages
985 - 988
Database
ISI
SICI code
0957-4166(1996)7:4<985:FSOBEO>2.0.ZU;2-2
Abstract
A short and efficient synthesis of both 8-amino-7-oxopelargonic acid e nantiomers from D or L-alanine is presented, The key step of this firs t chemical synthesis is the nonracemizing Horner-Wadsworth-Emmons reac tion of a beta-ketophosphonate 3 and benzyl 4-formylbutanoate. The gro wth-promoting effect of the enantiomers was tested on Saccharomyces ce revisiae. Copyright (C) 1996 Elsevier Science Ltd