Stereogenic Evolution of clasto??Lactacystin β??Lactone from L??Serine

CH Yoon, DL Flanigan, KS Yoo…

Index: Yoon, Cheol H.; Flanigan, David L.; Yoo, Kyung S.; Jung, Kyung W. European Journal of Organic Chemistry, 2007 , # 1 p. 37 - 39

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Citation Number: 15

Abstract

Abstract Reported herein is a novel synthesis of clasto-lactacystin β-lactone. The γ-lactam core was selectively prepared by an intramolecular C–H insertion to establish the stereocenter, C (6). The ensuing construction of the quaternary C (5) and carbinol C (9) centers was facilitated by aldol with excellent stereoselection. All these new stereochemistries were induced by the inherent chirality of L-serine without employing ...