
TY  - JOUR
A1  - Grant, PK 
A1  - Hanton, LR 
A1  - Tsai, SF 
T1  - Intramolecular Rearrangements of Labda-8(17),14-dien-13-ol (Manool) Derivatives
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1985
VL  - 38
IS  - 10
SP  - 1461
EP  - 1470
KW  - 
UR  - https://doi.org/10.1071/CH9851461 
N2  - 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. 
ER  -

