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Issue 0, 1972
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Studies in terpenoid biosynthesis. Part VIII. The formation of the trichothecane nucleus

Abstract

The incorporation of [2-3H2]-, (4R)-[4-3H]-, and [5-3H2]-mevalonate, [2-3H]geranyl pyrophosphate, and [1-3H2]-and [2-3H]-farnesyl pyrophosphate into the trichothecane nucleus is described. The results define the manner of folding of the farnesyl pyrophosphate and exclude a γ-bisabolene intermediate in the biosynthesis. The central prenyl (4R)-[4-3H]-label is retained in the biosynthesis and is transferred to C-2 of the trichothecane. The relative numbers of [2-3H2]- and [5-3H2]-mevalonoid labels that are incorporated suggest that the carbonyl group of trichothecin might arise through the rearrangement of an epoxide.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1972, 1425-1428
Article type
Paper

Studies in terpenoid biosynthesis. Part VIII. The formation of the trichothecane nucleus

B. A. Achilladelis, P. M. Adams and J. R. Hanson, J. Chem. Soc., Perkin Trans. 1, 1972, 1425
DOI: 10.1039/P19720001425

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