Total syntheses of natural tubelactomicins B, D, and E: Establishment of their stereochemistries

Kiyoto Sawamura, Keigo Yoshida, Akari Suzuki, Toru Motozaki, Ikuko Kozawa, Takashi Hayamizu, Ryosuke Munakata, Ken Ichi Takao, Kin Ichi Tadano

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Abstract

(Chemical Equation Presented) Total syntheses of the antimicrobial tricyclic 16-membered macrolides, (+)-tubelactomicin B, (+)-tubelactomicin D, and (+)-tubelactomicin E, have been accomplished for the first time with common synthetic approaches. These total syntheses established the relative and absolute configurations of the three tubelactomicins, for which planar structures had solely been reported. The total synthesis of (+)-tubelactomicin D included a newly developed stereoselective intramolecular Diels-Alder reaction for constructing the highly functionalized octahydronaphthalene substructures.

Original languageEnglish
Pages (from-to)6143-6148
Number of pages6
JournalJournal of Organic Chemistry
Volume72
Issue number16
DOIs
Publication statusPublished - 2007 Aug 1

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Sawamura, K., Yoshida, K., Suzuki, A., Motozaki, T., Kozawa, I., Hayamizu, T., Munakata, R., Takao, K. I., & Tadano, K. I. (2007). Total syntheses of natural tubelactomicins B, D, and E: Establishment of their stereochemistries. Journal of Organic Chemistry, 72(16), 6143-6148. https://doi.org/10.1021/jo0708442