Total synthesis of (+)-spiculoic acid A

Daisuke Matsumura, Takumi Toda, Takashi Hayamizu, Kiyoto Sawamura, Kenichi Takao, Kin ichi Tadano

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereoselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton.

Original languageEnglish
Pages (from-to)3356-3358
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 2009 Jul 1

Fingerprint

Polyketides
Cycloaddition Reaction
Biological Products
Skeleton
Derivatives
spiculoic acid A

Keywords

  • (+)-Spiculoic acid A
  • Cytotoxicity
  • Intramolecular Diels-Alder reaction
  • Marine natural product
  • Suzuki-Miyaura coupling
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Matsumura, D., Toda, T., Hayamizu, T., Sawamura, K., Takao, K., & Tadano, K. I. (2009). Total synthesis of (+)-spiculoic acid A. Tetrahedron Letters, 50(26), 3356-3358. https://doi.org/10.1016/j.tetlet.2009.02.101

Total synthesis of (+)-spiculoic acid A. / Matsumura, Daisuke; Toda, Takumi; Hayamizu, Takashi; Sawamura, Kiyoto; Takao, Kenichi; Tadano, Kin ichi.

In: Tetrahedron Letters, Vol. 50, No. 26, 01.07.2009, p. 3356-3358.

Research output: Contribution to journalArticle

Matsumura, D, Toda, T, Hayamizu, T, Sawamura, K, Takao, K & Tadano, KI 2009, 'Total synthesis of (+)-spiculoic acid A', Tetrahedron Letters, vol. 50, no. 26, pp. 3356-3358. https://doi.org/10.1016/j.tetlet.2009.02.101
Matsumura D, Toda T, Hayamizu T, Sawamura K, Takao K, Tadano KI. Total synthesis of (+)-spiculoic acid A. Tetrahedron Letters. 2009 Jul 1;50(26):3356-3358. https://doi.org/10.1016/j.tetlet.2009.02.101
Matsumura, Daisuke ; Toda, Takumi ; Hayamizu, Takashi ; Sawamura, Kiyoto ; Takao, Kenichi ; Tadano, Kin ichi. / Total synthesis of (+)-spiculoic acid A. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 26. pp. 3356-3358.
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