The first total synthesis of concanamycin F (concanolide A)

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

研究成果: Article

59 引用 (Scopus)

抜粋

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.

元の言語English
ページ(範囲)1708-1715
ページ数8
ジャーナルJournal of Organic Chemistry
66
発行部数5
DOI
出版物ステータスPublished - 2001 3 9

ASJC Scopus subject areas

  • Organic Chemistry

フィンガープリント The first total synthesis of concanamycin F (concanolide A)' の研究トピックを掘り下げます。これらはともに一意のフィンガープリントを構成します。

  • これを引用

    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