Vallartanone B: Synthesis and related studies

Hirokazu Arimoto, Rieko Yokoyama, Kazuhiko Nakamura, Yasuaki Okumura, Daisuke Uemura

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The synthesis of vallartanone B, a γ-pyrone-containing polypoprionate from the marine mollusc Siphonaria maura, is described. A γ-pyrone moiety, which was constructed by PPh 3 -CCl 4 cyclization of a β-triketone, and a C1-C6 segment were joined by a Sn(OTf) 2 aldol reaction and converted to vallartanone B. This synthesis allows for revision of the stereochemistry at C8. A conformational analysis was performed using PM3 to examine the proposed interpretation of its CD spectrum.

Original languageEnglish
Pages (from-to)13901-13908
Number of pages8
JournalTetrahedron
Volume52
Issue number44
DOIs
Publication statusPublished - 1996 Oct 28
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Arimoto, H., Yokoyama, R., Nakamura, K., Okumura, Y., & Uemura, D. (1996). Vallartanone B: Synthesis and related studies. Tetrahedron, 52(44), 13901-13908. https://doi.org/10.1016/0040-4020(96)00852-6