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Communication | Regular issue | Vol 48, No. 4, 1998, pp.635-640
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8123
Stereochemical Change in the Lewis Acid-promoted Reaction of 2-Siloxypyrrole Derived from (L)-Glutamic Acid. Synthesis of a Lactacystin Analogue

Hidemitsu Uno,* Noboru Mizobe, Youtarou Yamaoka, and Noboru Ono

*Advanced Instrumentation Center for Chemical Analysis, Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan

Abstract

In the presence of BF3·OEt2, the reaction of (3R)-5-t-butyldimethylsiloxy-6-methyl-3-phenyl-1H-pyrrolo[1,2-c]oxazole (3) with aliphatic aldehydes in ether occurred stereoselectively to give the corresponding (3R,7aR,1’R)-isomers (4a and 6a) as the major products, while the similar reaction with aromatic aldehydes afforded the (3R,7aR, 1’S)-isomers (7b, 8b, and 9b) predominantly. The product (7b) from the reaction with benzaldehyde was successfully transformed to a lactacystin analogue.