Formal total synthesis of altohyrtin C (spongistatin 2). Part 1: Aldol approach to unite AB and CD spiroacetals

Takeshi Terauchi, Taro Terauchi, Ippei Sato, Wataru Shoji, Tomoharu Tsukada, Takashi Tsunoda, Naoki Kanoh, Masaya Nakata

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

The Mukaiyama aldol coupling of the second-generation C1-C14 (AB) fragment of altohyrtins (spongistatins) with the model α-methyl-β -alkoxyaldehydes revealed that the stereochemistry at the newly formed carbon centers was controlled by the β-alkoxy chiral center of the model aldehydes. The union of the AB fragment with the C15-C28 (CD) fragment under the same conditions gave the fully elaborated C1-C28 (ABCD) subunit in good yield.

Original languageEnglish
Pages (from-to)7741-7745
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number42
DOIs
Publication statusPublished - 2003 Oct 13

Keywords

  • Aldol reaction
  • Altohyrtins
  • Spongistatins
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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