Enantioselective Construction and Utilization of 2-(Cyclohex-2-enyl)phenols
31 December 2000 (online)
Enantioselective construction of 2-(cyclohex-2-enyl)phenols from chiral equivalents of cyclohex-2-enols has been investigated by employing a concurrent retro-Diels-Alder reaction and Claisen rearrangement protocol. Utilizing the enantiomerically pure product obtained, the first enantiocontrolled synthesis of a phenolic natural sesquiterpene (+)-curcudiol, isolated from the marine sponge Didiscus flavus, has been demonstrated.
chiral building block - chiral cyclohexenol equivalent - Mitsunobu reaction - Claisen rearrangement - retro-Diels-Alder reaction