Stereoselective synthesis of solanesol and all-trans-decaprenol

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).