Enantioselective total synthesis of (-)-scabronine D

Yu Kobayakawa, Masahisa Nakada

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The first enantioselective total synthesis of (-)-scabronine D comprising a unique bridged hemiacetal is described. The total synthesis is successfully accomplished using an enantiopure intermediate prepared in the total synthesis of (-)-scabronines G and A, and (-)-episcabronine A. Because the advanced intermediate was found to be sensitive to basic reaction conditions, the C14 keto and C11 hydroxy groups had to be co-protected as methyl acetal. In addition, both the C15 hydroxy and C17 carboxyl groups were too reactive to be chemically discriminated; hence, the carboxyl group once formed was protected as a tert-butyl ester for ensuring successful transformations.

Original languageEnglish
Pages (from-to)669-677
Number of pages9
JournalHeterocycles
Volume89
Issue number3
DOIs
Publication statusPublished - 2014

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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