Issue 0, 1981
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Stereoselective synthesis of solanesol and all-trans-decaprenol

Kikumasa Sato,   Seiichi Inoue,   Akira Onishi,   Nobuhiko Uchida  and  Nobuto Minowa  

Abstract

Allylic p-tolyl sulphones (5), (14), and (16) couple with allylic bromide (7) and geranyl bromide to produce regio- and stereo-chemically pure 1,5-diene systems. The coupling of all-trans-ω-bromogeranyl acetate (7) with geranyl p-tolyl sulphone (5) and higher isoprenologues (21), (24), and (27), followed by reductive elimination of p-tolysulphonyl group, furnishes a stereoselective synthesis of all-trans-polyprenols (3), (23),(26), and decaprenol (1b). Solanesol (1a) was synthesised using trans-4-chloroprenyl acetate (29) instead of (7).

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Article information

DOI
https://doi.org/10.1039/P19810000761
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 761-769

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Stereoselective synthesis of solanesol and all-trans-decaprenol

K. Sato, S. Inoue, A. Onishi, N. Uchida and N. Minowa, J. Chem. Soc., Perkin Trans. 1, 1981, 761 DOI: 10.1039/P19810000761

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