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

研究成果: Article査読

5 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)230-233
ページ数4
ジャーナルOrganic Letters
19
1
DOI
出版ステータスPublished - 2017 1 6
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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