Model studies of the biosynthesis of non-head-to-tail terpenes. Stereochemistry of the head-to-head rearrangement

CD Poulter, JM Hughes

Index: Poulter,C.D.; Hughes,J.M. Journal of the American Chemical Society, 1977 , vol. 99, # 11 p. 3830 - 3837

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Citation Number: 23

Abstract

Abstract: The stereochemistry of the head-to-head rearrangement which occurs during biosynthesis of squalene from presqualene pyrophosphate was studied with a ten-carbon model system, N-methyl-4-[(lS, 1'R, 3'R)-[l-3H] chrysanthemyloxy] pyri-dinium iodide, in a nonenzymatic reaction. A head-to-head product,[5-3H]-2, 7-dimethylocta-2, 6-dien-4-ol, is isolated after hydrolysis. The absolute configuration at C (5) was determined by converting ...