Derivatives of 8-dehydro-vitamin a and their preparation

Details Derivatives of 8-dehydro-vitamin a and their preparation Derivatives of 8-dehydro-vitamin a and their preparation

C - Chemistry, Metallurgy

07

C

260/395, 260/493

C07C 23/10 (2006.01) C07F 9/54 (2006.01) C07C 175/00 (1980.01)

Patent

CA 1111054

ABSTRACT OF THE DISCLOSURE: New derivatives of d-dehydro-vitamin A obtained by vinylating or ethynylating and subsequently partially hydrogenating 1-[3-methyl-octa-1-yne-3,5-dien-7-on-1-yl]-2,6- -dimethyl-cyclohex-1-ene or its 5- and/or 6-methyl derivatives, converting the resulting alcohols to the corresponding derivatives of 8-dehydro-vitamin A halides by reacting with thionyl chloride or phosgene, and if required converting the resulting alcohols or halides to the corresponding trialkylphosphonium salts or triaryl- phosphonium salts, or reacting the 8-dehydro-vitamin A halide derivatives with alkali metal salts or alkaline earth metal salts or anhydrides of lower carboxylic acids. The new compounds can be partially hydrogenated to the corresponding polyene compounds, in which case the cis-trans isomer mixtures first obtained can be rearranged in the conventional manner to the physiologically active all-trans compounds. Accordingly, the process provides a method for the total synthesis of vitamin A, and of other com- pounds or the carotinoid series, which is independent of the Wittig ylide synthesis.

301167

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