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Efficient synthesis of (1R, 4S, 6R)-4-Isopropenyl-1, 3, 3-trimethyl-7-oxabicyclo [4.1. 0] heptan-2-one

NK Selezneva, FA Gimalova, RF Valeev…

文献索引:Selezneva; Gimalova; Valeev; Miftakhov Russian Journal of Organic Chemistry, 2011 , vol. 47, # 2 p. 173 - 179

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被引用次数: 0

摘要

Abstract A simple and convenient one-pot synthesis of (1 R, 4 S, 6 R)-4-isopropenyl-1, 3, 3- trimethyl-7-oxabicyclo [4.1. 0] heptan-2-one was developed consisting in a thermodynamic methylation of carvone (NaH, MeI, THF, 20° C) followed by the epoxidation with alkalinized hydrogen peroxide. The reduction of the obtained epoxyketone with sodium borohydride proceeded stereoselectively to give a β-alcohol. The attempts to convert its isopropenyl ...