68731-63-5Relevant articles and documents
An improved convergent strategy for the synthesis of oligoprenols
Yu, Xiong-Jie,Zhang, Hao,Xiong, Fang-Jun,Chen, Xu-Xiang,Chen, Fen-Er
experimental part, p. 1967 - 1974 (2009/02/07)
A practical and highly regio- and stereoselective synthesis of oligoprenols starting from commercially available geraniol is described. The convergent synthetic strategy features the iterative allyl-allyl coupling of monomers easily derived from geraniol that contain one reacting terminal functional group and the repetitive reductive elimination of the p-toluenesulfonyl (Ts) groups.
Stereoselective Synthesis of Solanesol and all-trans-Decaprenol
Sato, Kikumasa,Inoue, Seiichi,Onishi, Akira,Uchida, Nobuhiko,Minowa, Nobuto
, p. 761 - 769 (2007/10/02)
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).