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

1979-01-12

1981-06-09

Sneed, Helen M. S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Halogen containing

568 9, 568824, C07C 2102, C07F 954

Patent

active

042724562

ABSTRACT:
New derivatives of 8-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 triarylphosphonium 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 compounds of the carotinoid series, which is independent of the Wittig ylide synthesis.

REFERENCES:
patent: 2809216 (1957-10-01), Inhoffen
patent: 2842599 (1958-07-01), Isler et al.
patent: 2912474 (1959-11-01), Oroshnik
patent: 4014946 (1977-03-01), Labovitz et al.
patent: 4075257 (1978-02-01), Close et al.

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