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, Kenichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

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

Fingerprint

Polyketides
Biological Products
Acids
Cycloaddition Reaction
Skeleton
Isomers
Derivatives
spiculoic acid A

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin. / Matsumura, Daisuke; Takarabe, Toshimasa; Toda, Takumi; Hayamizu, Takashi; Sawamura, Kiyoto; Takao, Kenichi; Tadano, Kin Ichi.

In: Tetrahedron, Vol. 67, No. 35, 02.09.2011, p. 6730-6745.

Research output: Contribution to journalArticle

Matsumura, D, Takarabe, T, Toda, T, Hayamizu, T, Sawamura, K, Takao, K & Tadano, KI 2011, 'Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin', Tetrahedron, vol. 67, no. 35, pp. 6730-6745. https://doi.org/10.1016/j.tet.2011.04.006
Matsumura, Daisuke ; Takarabe, Toshimasa ; Toda, Takumi ; Hayamizu, Takashi ; Sawamura, Kiyoto ; Takao, Kenichi ; Tadano, Kin Ichi. / Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin. In: Tetrahedron. 2011 ; Vol. 67, No. 35. pp. 6730-6745.
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