A NOVEL SKELETAL REARRANGEMENT OF BICYCLO(2.2.2)OCTENES THROUGH BICYCLO(3.2.1)OCTENE SYSTEM: SYNTHESIS OF (+/-)-HINESOL AND (+/-)-10-epi-HINESOL

Article abstract of DOI:10.1016/0040-4039(88)85097-4

Acid catalysed rearrangement of the endo-alcohol (9) leads to the ketones (11) and (12) having the bicyclo(3.2.1) and bicyclo(2.2.2) moieties.An efficient entry into spiro(4,5)decane and eremane system, as exemplified by the total synthesis of (+/-)-hinesol (2) and its 10-epimer (3) is reported.