Enantioselective total synthesis of (+)-bucidarasins A and C

Kenji Usui, Masahisa Nakada

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

In this paper, the first total synthesis of (+)-bucidarasins A and C is described. The chiral starting material was successfully obtained via reduction using a CBS catalyst and selective mono-TBS ether formation of trans -2-benzyloxymethyl-2-methylcyclohexane-1,3-diol, which was crucial to the successful enantioselective total synthesis of (+)-bucidarasins A and C. A synthetic approach towards (+)-bucidarasin C, based on the Barton-McCombie protocol, using V-70 as a radical promoter at low temperature to remove the C6-hydroxy moiety is also described.

Original languageEnglish
Pages (from-to)332-350
Number of pages19
JournalHeterocycles
Volume91
Issue number2
DOIs
Publication statusPublished - 2015

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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