Author:
Cambie Richard C.,Davy Perry K.,Mitchell Lorna H.,Rickard Clifton E. F.,Rutledge Peter S.
Abstract
The radical decarboxylation–sulfoxide cycloelimination of
2′-pyridylthio esters formed from a series of podocarpic acid
derivatives gives Δ4(18) -alkenes in high yield.
An exception is the 13-nitro acid (2) which affords a thiohydroxamic ester
(28), the relative stability of which is attributed to inhibition of the
radical chain reaction by the nitro group. The stereochemistry of the pyridyl
sulfide (18) has been confirmed by X-ray crystallography.
Cited by
4 articles.
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