Jump to main content
Jump to site search

Issue 8, 1990
Previous Article Next Article

Synthesis of marine toxins. A biomimetic approach to the novel spirobenzoquinonefuran stypoldione

Abstract

A synthesis of the spirobenzoquinonefuran unit, i.e.(10), present in stypoldione, a novel marine toxin found in the brown alga Stypopodium zonale which shows pronounced narcotic and hyperactive effects upon reef-dwelling fish, is described. The synthesis uses a strategy, viz(17)→(18)→(19)→(11)→(10), which has close similarities to the probable biogenesis of this portion of the natural product (scheme 1). The advanced precursors (30) and (36) for projected syntheses of deoxystypoldione (33) and stypodiol (3) respectively were also prepared, but neither substrate underwent polyene cyclization to the required pentacyclic molecules.

Back to tab navigation

Article type: Paper
DOI: 10.1039/P19900002263
J. Chem. Soc., Perkin Trans. 1, 1990, 2263-2271

  •   Request permissions

    Synthesis of marine toxins. A biomimetic approach to the novel spirobenzoquinonefuran stypoldione

    M. J. Begley, P. V. Fish, G. Pattenden and S. T. Hodgson, J. Chem. Soc., Perkin Trans. 1, 1990, 2263
    DOI: 10.1039/P19900002263

Search articles by author

Spotlight

Advertisements