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Synthesis of (R,S)-(5Z,8E,10E)-12-Hydroxyheptadeca-5,8,10-trienoic Acid and of (R,S) and (S)-(5Z,8Z,10E,14Z)-12-Hydroxyeicosa-5,8,10,14-tetraenoic Acid and their Racemic 5,6,8,9-tetradeuterioisomers

DOI: 10.1039/P19820000545

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 545 - 552 (1982)

Update date:2022-08-17

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Authors:

Russel, Stephen W.Russel, Stephen W.

Pabon, Henk J. J.Pabon, Henk J. J.

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Article abstract of DOI:10.1039/P19820000545

(5Z,8Z,10E,14E)-12-Hydroxyeicosa-5,8,10,14-tetraenoic acid <(S) and (R,S)-enantiomers >, (R,S)-(5Z,8Z,10E,14Z)-12-hydroxy-5,6,8,9-tetradeuterio-5,8,10,14-tetraenoic acid, (R,S)-(5Z,8E,10E)-12-hydroxyheptadeca-5,8,10-trienoic acid, and (R,S)-(5Z,8E,10E)-12-hydroxy-5,6,8,9-tetradeuterioheptadeca-5,8,10-trienoic acid have been prepared by total synthesis.Deuterium was introduced at selected sites by partial reduction.All the acids were prepared from the common intermediate ethyl 10,10-diethoxydeca-5,8-dienoate.The c.d. spectrum of (S)-(7h) confirmed its identity with the natural product.The mechanism of the reaction of heptynyl-lithium with (S)-1-chloro-2,3-epoxypropane has been shown to be by attack on the epoxide group, with subsequent recyclisation of the chloroalkoxide to give (S)-1,2-epoxydec-4-yne.

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