Vitamin A synthesis by sulfone alkylation-elimination. C15 halide, C5 hydroxy sulfone approach

…, HC Cheung, KD Morgan, C Neukom…

文献索引：Olson; Cheung; Morgan; Neukom; Saucy Journal of Organic Chemistry, 1976 , vol. 41, # 20 p. 3287 - 3293

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被引用次数: 62

摘要

Condensation of l-arylsulfonyl-2-methyl-4-hydroxy-2-butenes (1) with 1-chloro-and l-bromo- 3-methyl-5-(2, 6, 6-trimethylcyclohexen-l-yl)-penta-2, 4-diene (2) to afford l-hydroxy-3, 7- dimethyl-4-arylsulfonyl-9-(2, 6, 6-trimethylcyclohexen-l-yl) nona-2, 6, 8-triene (3) and the subsequent elimination of sulfinic acid from 3 to give vitamin A alcohol has been studied. An efficient and stereoselective synthesis of halide 2 from vinyl-P-ionol (l4) using HX in ether ...