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Studies in terpenoid biosynthesis. Part IV. Biosynthesis of the kaurenolides and gibberellic acid

Studies in terpenoid biosynthesis. Part IV. Biosynthesis of the kaurenolides and gibberellic acid Geranylgeraniol and (–)-labda-8,13-dien-15-ol pyrophosphate have been shown to act as precursors of (–)-kaurene, the kaurenolides, and gibberellic acid. The labelling pattern from 4-()-[4-H]- and 2-[H]-mevalonic acid in these tetracyclic diterpenes has been determined and this evidence is used to exclude (–)-primara-7,8- and -8,9-dienes from the biosynthesis. (–)Pimara-8(14)-diene has been shown to be specifically incorporated into the kaurenolides and gibberellic acid. The stereochemistry of hydroxylation of ring A of the gibberellins has been shown to proceed with retention of configuration. The loss of the angular C-20 atom in the formation of the C-19 gibberellins does not involve the decarboxylation of a 4-, 4b-, or 10a-unsaturated acid. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of the Chemical Society C Organic Royal Society of Chemistry

Studies in terpenoid biosynthesis. Part IV. Biosynthesis of the kaurenolides and gibberellic acid

Hanson, J. R.; White, A. F.
Royal Society of Chemistry — Jan 1, 1969
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Royal Society of Chemistry
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Abstract

Geranylgeraniol and (–)-labda-8,13-dien-15-ol pyrophosphate have been shown to act as precursors of (–)-kaurene, the kaurenolides, and gibberellic acid. The labelling pattern from 4-()-[4-H]- and 2-[H]-mevalonic acid in these tetracyclic diterpenes has been determined and this evidence is used to exclude (–)-primara-7,8- and -8,9-dienes from the biosynthesis. (–)Pimara-8(14)-diene has been shown to be specifically incorporated into the kaurenolides and gibberellic acid. The stereochemistry of hydroxylation of ring A of the gibberellins has been shown to proceed with retention of configuration. The loss of the angular C-20 atom in the formation of the C-19 gibberellins does not involve the decarboxylation of a 4-, 4b-, or 10a-unsaturated acid.

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Journal of the Chemical Society C Organic – Royal Society of Chemistry

Published: Jan 1, 1969

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