Formal synthesis of tubelactomicins via a transannular Diels-Alder approach

Toshimi Anzo, Akari Suzuki, Kiyoto Sawamura, Toru Motozaki, Madoka Hatta, Ken ichi Takao, Kin ichi Tadano

研究成果: Article査読

14 被引用数 (Scopus)

抄録

A formal synthesis of the antimicrobial tricyclic macrolides, tubelactomicins A and E, featured by a transannular Diels-Alder (TADA) approach, has been explored. The key issue for the transannular cyclization was the synthesis of a 24-membered macrolactone equipped with all the requisite functionalities, which has been achieved using an intramolecular Hiyama cross-coupling strategy. The Hiyama coupling reaction spontaneously triggered off the TADA reaction. From the endo-TADA adduct, formal syntheses of tubelactomicins A and E were achieved. The 24-membered macrolactone formation was also achieved via an intramolecular ring-closing metathesis approach.

本文言語English
ページ(範囲)8442-8448
ページ数7
ジャーナルTetrahedron Letters
48
48
DOI
出版ステータスPublished - 2007 11 26

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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