Studies in terpenoid biosynthesis. Part VI. The stereochemistry of some stages in tetracyclic diterpene biosynthesis
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 18,p. 2601-2603
- https://doi.org/10.1039/j39700002601
Abstract
The stereospecific labelling of the gibberellins and the kaurenolides with 2-(R)-, 2-(S)- and 5-(R)-[3H]mevalonate has been studied. The results lead to the conclusion that the dehydrogenation of ring A in gibberellic acid bio-synthesis is a cis-process and that the hydroxylation of ring B in the formation of the kaurenolides takes place with retention of configuration. One tritium atom from [1-3H2,2-14C]geranyl pyrophosphate is retained at position 10 in gibberellic acid. However 5-(R)-mevalonoid hydrogen is lost from ring B during the formation of the gibberellins. Consequently ring contraction takes place with the displacement of an equatorial hydrogen atom from the kauranoid C-6-position.Keywords
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