Calciferol and its relatives. Part XVII. Ring-A components for synthetic work on vitamin D3 and on model compounds

1 January 1974

journal article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1

No. 17,p. 2005-2009
https://doi.org/10.1039/p19740002005

Abstract

Optically active (S)-(Z)-2-(5-hydroxy-2-methylenecyclohexylidene)ethanol (6), which is of interest as a ring-A component for a possible synthesis of vitamin D₃, has been prepared from vitamin D₂. Its simpler analogue (Z)-2-(2-methylenecyclohexylidene)ethanol (9) has been synthesised by two routes. In the more efficient, the βγ-unsaturated lactone 3-oxabicyclo[4.4.0]dec-1(6)-en-4-one (14) was converted by treatment with lithium diisopropylamide into (Z)-(2-methylenecyclohexylidene)acetic acid (30), which was then reduced to the dienol (9).

Keywords

TREATMENT
UNSATURATED LACTONE
MODEL COMPOUNDS
SIMPLER ANALOGUE
ACETIC ACID
OPTICALLY ACTIVE
PART XVII
SYNTHETIC WORK

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