AN EPOXIDE-BASED ENANTIOSELECTIVE SYNTHESIS OF THE ANTIFUNGAL ANTIBIOTIC (-PREUSSIN())

Authors
BEIER C SCHAUMANN E
Citation
C. Beier et E. Schaumann, AN EPOXIDE-BASED ENANTIOSELECTIVE SYNTHESIS OF THE ANTIFUNGAL ANTIBIOTIC (-PREUSSIN()), Synthesis, (11), 1997, pp. 1296-1300
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
11
Year of publication
1997
Pages
1296 - 1300
Database
ISI
SICI code
0039-7881(1997):11<1296:AEESOT>2.0.ZU;2-P
Abstract
The enantioselective total synthesis of -1-methyl-5-nonyl-2-(phenylmet hyl)-3-pyrrolidinol, (+)-preussin 1, from (S)-phenylalanine is describ ed. Key steps involve ring-opening of a (1-aminoalkyl) epoxide 5 by an allyl anion, [2,3]-sigmatropic rearrangement of 9 and cyclization of aminoepoxide 11 to give the pyrrolidine unit 12 with the correct stere ochemistry.