Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin

Daisuke Matsumura, Toshimasa Takarabe, Takumi Toda, Takashi Hayamizu, Kiyoto Sawamura, Ken Ichi Takao, Kin Ichi Tadano

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5 Citations (Scopus)

Abstract

The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels-Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton. A stereocongener of (+)-spiculoic acid A, i.e., the (2R,5S,6R)-isomer, was also synthesized. The details of these total syntheses are described.

Original languageEnglish
Pages (from-to)6730-6745
Number of pages16
JournalTetrahedron
Volume67
Issue number35
DOIs
Publication statusPublished - 2011 Sep 2

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Keywords

  • (+)-Spiculoic acid A
  • (+)-Zyggomphic acid
  • Cytotoxicity
  • Intramolecular reaction Diels-Alder reaction
  • Marine natural product

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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