Total synthesis of (-)-bucidarasin a starting from an original chiral building block

Kenji Usui, Misaki Kanbe, Masahisa Nakada

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The highly stereoselective total synthesis of (-)-bucidarasin A, which also elucidated the absolute structure of its natural form, is described. The total synthesis features effective use of the original chiral building block prepared by us and a series of highly stereoselective reactions, i.e., hydroxydirected hydrogenation, [4 + 2] cycloaddition of a sterically hindered dienophile, reduction of ketones, formation of the C9 side-chain diene, and formation of the THF moiety bearing two acetyloxy groups.

Original languageEnglish
Pages (from-to)4734-4737
Number of pages4
JournalOrganic Letters
Volume16
Issue number18
DOIs
Publication statusPublished - 2014 Sep 19
Externally publishedYes

Fingerprint

Hydrogenation
Cycloaddition Reaction
Ketones
Bearings (structural)
Cycloaddition
cycloaddition
dienes
synthesis
ketones
hydrogenation
bucidarasin A

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Total synthesis of (-)-bucidarasin a starting from an original chiral building block. / Usui, Kenji; Kanbe, Misaki; Nakada, Masahisa.

In: Organic Letters, Vol. 16, No. 18, 19.09.2014, p. 4734-4737.

Research output: Contribution to journalArticle

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