On the thermal sigmatropic rearrangement of allenic retinoids: 12, 14-retro-retinol

J Sueiras, WH Okamura

Index: Sueiras; Okamura Journal of the American Chemical Society, 1980 , vol. 102, # 20 p. 6255 - 6259

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Citation Number: 13

Abstract

Abstract: The 11, 12-allenic retinoid 7 (Y= CH20Si (CH3),-t-Bu) was synthesized in 51% yield by Wittig condensation of the ylide of P-ionyltriphenylphospnium bromide (12) with the allenic aldehyde 1Oc. The latter was synthesized from isopentenyl alcohol 8a in four steps (53% overall). Thermolysis of 7 (Y= CH20Si (CH3) 2-t-Bu) afforded a-1.9: 1 ratio of the double bond shifted retinoid (a retro-ene isomer) 13a and a mixture of retinol ethers (-2: 1 ...