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Stereoselective Syntheses of Tetrahydroesterastin‐β ‐Lactam Analogues
Author(s) -
Huber Isabelle,
Schneider Fernand
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770420
Subject(s) - chemistry , stereoselectivity , lactam , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
A total synthesis of the optically active tetrahydroesterastin β ‐lactam analogue 2 using Miller 's hydroxamate approach is described ( Scheme 2 ). Significant modification of published procedures has resulted in a short and facile stereospecific preparation of the N ‐[(benzyloxycarbonyl)methyl]‐β ‐lactam 17 starting from the readily available D ‐serine. This material served as intermediate for the preparation of a variety of N ‐[(benzyloxycarbonyl)methyl]tetrahydroesterastin β‐lactam analogues ( Scheme 5 ).