Total synthesis of (+)-spiculoic acid A

Daisuke Matsumura, Takumi Toda, Takashi Hayamizu, Kiyoto Sawamura, Ken ichi 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

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Total synthesis of (+)-spiculoic acid A'. Together they form a unique fingerprint.

  • Cite this

    Matsumura, D., Toda, T., Hayamizu, T., Sawamura, K., Takao, K. I., & 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