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Communication | Regular issue | Vol 81, No. 10, 2010, pp.2239-2246
Published online, 26th August, 2010
DOI: 10.3987/COM-10-12042
An Enantio- and Diastereocontrolled Synthesis of (–)-Salinosporamide A

Yosuke Sato, Hayato Fukuda, Masaki Tomizawa, Tomohito Masaki, Masatoshi Shibuya, Naoki Kanoh, and Yoshiharu Iwabuchi*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

The enantio- and diastereocontrolled total synthesis of (–)-salinosporamide A, a potent 20S proteasome inhibitor, was accomplished through organocatalytic aldolization, diastereoselective Claisen condensation, a Rh-catalyzed Reformatsky reaction, and an AZADO-catalyzed oxidative β-lactonization reaction as the key reactions.