Asymmetric Formal Synthesis of (+)-Lactacystin

作者:Sridhar Chirumarry; Vijaykumar Bodduri V D; Radhika Laghuvarapu; Shin Dong Soo*; Chandrasekhar Srivari
来源:European Journal of Organic Chemistry, 2014, 2014(30): 6707-6712.
DOI:10.1002/ejoc.201402700

摘要

A formal synthesis of (+)-lactacystin was achieved from commercially available isobutyraldehyde and ethyl acrylate. A Baylis-Hillman reaction, an intermolecular nucleophilic displacement under Mitsunobu conditions, a Sharpless asymmetric epoxidation, a palladium(0)-catalyzed syn-selective ring opening of an epoxide by treatment with an azide, a one-pot azide reductive lactamization, and a ruthenium-catayzed oxidation were employed as the key steps.

  • 出版日期2014-10