The Journal of Organic Chemistry

Vitamin D (calciferol) and its analogs. 19. Rearrangement of vinylallenes to 1-hydroxylated vitamin D model systems lacking the D ring and side chain

P Condran Jr, WH Okamura

Index: Condran, Patrick; Okamura, William H. Journal of Organic Chemistry, 1980 , vol. 45, # 20 p. 4011 - 4015

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Citation Number: 11

Abstract

The therrnally induced sigmatropic shifts of vinylallenone 7 and vinylallenol8 were studied. The former (7) rearranges (-100" C, 18 h) to previtamin ketone model system 13 in essentially quantitative yield; further thermolysis (-180" C, 10 h) of 13 afforded pyrocalciferone analogue 14 (57%) and a new member of the vitamin D thermal manifold, spiro ketone 15 (17%). Thermolysis of the alcohol 8 at-100" C (8 h) afforded what was ...

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