Studies in terpenoid biosynthesis. Part 26. Applications of 2H and 13C n.m.r. spectroscopy to the biosynthesis of the illudin sesquiterpenoids
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2445-2448
- https://doi.org/10.1039/p19820002445
Abstract
The 13C n.m.r. resonances of the illudins have been assigned. The labelling pattern of illudin M and illudin S derived from [1,2-13C2]acetate and the induced coupling between C-6 and C-7 in samples biosynthesized from [1-13C]acetate are in accord with the previous dissection of the carbon skeleton into isoprene units. The enrichment from [2-2H3]acetate and [2-2H2]mevalonate indicates that one mevalonoid label is lost from C-12 during the biosynthesis. The retention of a 2H–13C coupling at H-6 in illudin M which was biosynthesized from [5-2H2,5-13C]mevalonate shows that this hydrogen atom is not involved in a hydride rearrangement in contrast to previous conclusions.Keywords
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