The first total synthesis of concanamycin F (concanolide A)

K. Toshima, T. Jyojima, N. Miyamoto, M. Katohno, M. Nakata, S. Matsumura

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Abstract

A highly stereoselective total synthesis of the macrolide antibiotic concanamycin F (1), a specific and potent inhibitor of vacuolar H+-ATPase, has been achieved by a convergent route involving the synthesis and coupling of its 18-membered tetraenic lactone and β-hydroxyl hemiacetal side chain subunits. The C1-C19 18-membered lactone aldehyde 4 was synthesized through the intermolecular Stille coupling of the C5-C13 vinyl iodide 24 and the C14-C19 vinyl stannane 25, followed by construction of the C1-C4 diene and macrolactonization. Synthesis of 4 via a second convergent route including the esterification of the C1-C13 vinyl iodide 45 and the C14-C19 vinyl stannane 47 followed by the intramolecular Stille coupling was also realized. The highly stereoselective aldol coupling of 4 and the C20-C28 ethyl ketone 5 followed by desilylation provided 1 which was identical with natural concanamycin F.

Original languageEnglish
Pages (from-to)1708-1715
Number of pages8
JournalJournal of Organic Chemistry
Volume66
Issue number5
DOIs
Publication statusPublished - 2001 Mar 9

ASJC Scopus subject areas

  • Organic Chemistry

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    Toshima, K., Jyojima, T., Miyamoto, N., Katohno, M., Nakata, M., & Matsumura, S. (2001). The first total synthesis of concanamycin F (concanolide A). Journal of Organic Chemistry, 66(5), 1708-1715. https://doi.org/10.1021/jo001377q