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

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13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8442-8448
Number of pages7
JournalTetrahedron Letters
Volume48
Issue number48
DOIs
Publication statusPublished - 2007 Nov 26

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Keywords

  • Hiyama coupling
  • Macrolide antibiotics
  • Ring-closing olefin metathesis
  • Transannular Diels-Alder reaction
  • Tubelactomicins

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Anzo, T., Suzuki, A., Sawamura, K., Motozaki, T., Hatta, M., Takao, K. I., & Tadano, K. I. (2007). Formal synthesis of tubelactomicins via a transannular Diels-Alder approach. Tetrahedron Letters, 48(48), 8442-8448. https://doi.org/10.1016/j.tetlet.2007.10.002