Journal of the Chemical Society. Perkin transactions I p. 761 - 769 (1981)
Update date:2022-08-04
Topics:
Sato, Kikumasa
Inoue, Seiichi
Onishi, Akira
Uchida, Nobuhiko
Minowa, Nobuto
Allylic p-tolyl sulphonates (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-tolylsulphonyl 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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Doi:10.1016/S0022-328X(00)85520-5
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