Synthetic studies on altohyrtins (spongistatins): Synthesis of the C29-C44 (EF) portion

Takeshi Terauchi, Masataka Morita, Kyoko Kimijima, Yasuhiro Nakamura, Gouichirou Hayashi, Taisaku Tanaka, Naoki Kanoh, Masaya Nakata

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The C29-C44 portion of altohyrtins (spongistatins) has been prepared from 1,5-pentanediol and D-glucose in a stereoselective manner. The convergent synthesis relied on a coupling reaction of the C29-C37 vinyl bromide and the C38-C44 Weinreb amide, diastereoselective reduction of the C38 ketone, and stereoselective formation of the C33-C37 (E ring) acetal.

Original languageEnglish
Pages (from-to)5505-5508
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number32
DOIs
Publication statusPublished - 2001 Aug 6

Keywords

  • Altohyrtins
  • Spongistatins
  • Stereoselective synthesis
  • Weinreb coupling

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Terauchi, T., Morita, M., Kimijima, K., Nakamura, Y., Hayashi, G., Tanaka, T., Kanoh, N., & Nakata, M. (2001). Synthetic studies on altohyrtins (spongistatins): Synthesis of the C29-C44 (EF) portion. Tetrahedron Letters, 42(32), 5505-5508. https://doi.org/10.1016/S0040-4039(01)01069-3