Efficient, enantioselective organocatalytic synthesis of trichostatin A

Shilei Zhang, Wenhu Duan, Wei Wang

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

An efficient, highly stereocontrolled total synthesis of trichostatin A (1) has been achieved in 9 steps with 17.4% overall yield and >99% optical purity from readily available achiral starting materials. The key features of this synthesis include the L-proline-promoted, highly enantioselective cross-aldol reaction as a crucial step for the construction of the C-6 chiral center and the minimization of racemization by final step oxidation of the OH group to a ketone at position 7.

Original languageEnglish (US)
Pages (from-to)1228-1234
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume348
Issue number10-11
DOIs
StatePublished - Jul 2006
Externally publishedYes

Keywords

  • Aldol reaction
  • Asymmetric organocatalysis
  • HDAC inhibitors
  • Proline
  • Trichostatin A

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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