
%0 Journal Article
%A Grant, PK 
%A Hanton, LR 
%A Tsai, SF 
%T Intramolecular Rearrangements of Labda-8(17),14-dien-13-ol (Manool) Derivatives
%J Australian Journal of Chemistry
%D 1985/10/01
%V 38
%N 10
%P 1461-1470
%K 
%R https://doi.org/10.1071/CH9851461
%U https://www.publish.csiro.au/paper/CH9851461 
%X The products of epoxidation of the enol ether 8,13-epoxy-17-norlabd-8-ene (2) arise from the acid-labile acetal nature of the expected epoxide. Acid-promoted 1,2-nucleophilic rearrangements of subsequently formed epoxides give rise to the isolated products, including the novel spiro hydroxy ketone 8&#946;,13-epoxy-7&#946;-hydroxy-10(9&#8594;8)abeo-17-norlabdan-9-one (8), the structure of which was determined by X-ray analysis of the acetate derivative. The structure of the major product, 8,13- epoxy-17-norlabd-8-en-7-one (5), was confirmed by synthesis. 
