An enantio-and diastereocontrolled synthesis of (-)-salinosporamide A

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

Research output: Contribution to journalReview articlepeer-review

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2239-2246
Number of pages8
JournalHeterocycles
Volume81
Issue number10
DOIs
Publication statusPublished - 2010 Dec 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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