Stereocontrolled synthesis of vitamin A through a double elimination reaction. A novel convergent C10+ C10 route

J Otera, H Misawa, T Onishi, S Suzuki…

Index: Otera; Misawa; Onishi; et al. Journal of Organic Chemistry, 1986 ,  vol. 51,  # 20  p. 3834 - 3838

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Citation Number: 39

Abstract

The first convergent Clo+ Clo route for vitamin A has been developed. The double elimination reaction of p-alkoxy or &halo sulfones proceeds with excellent stereocontrol to afford the all-trans and 13-cis isomers of W95% purity. The double elimination reaction of P- alkoxy sulfones is initiated by deprotonation of an allylic hydrogen in 9, while the reaction of &halo sulfones proceeds through the Michael addition of potassium methoxide. ...