Total synthesis and determination of the absolute configuration of naturally occurring mangromicin A, with potent antitrypanosomal activity

Hirokazu Takada, Takeshi Yamada, Tomoyasu Hirose, Takuma Ishihara, Takuji Nakashima, Yoko Takahashi, Satoshi Omura, Toshiaki Sunazuka

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

An enantioselective total synthesis of (+)-mangromicin A has been accomplished. The tetrahydrofuran ring of mangromicin A, possessing a tetrasubstituted carbon center, was constructed by Mukaiyama-type vinylogous alkylation via a cyclic oxocarbenium intermediate derived from a γ-hydroxy ketone with ideal stereoselectivity, and the 4-hydroxydihydropyrone scaffold was generated via Dieckmann cyclization at a late stage of the total synthesis. The reliable asymmetric synthesis of (+)-mangromicin A has revealed the absolute configuration of naturally occurring mangromicin A.

Original languageEnglish
Pages (from-to)230-233
Number of pages4
JournalOrganic Letters
Volume19
Issue number1
DOIs
Publication statusPublished - 2017 Jan 6
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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