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Synlett 1998; 1998(9): 1004-1006
DOI: 10.1055/s-1998-1844
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Enantioselective Construction and Utilization of 2-(Cyclohex-2-enyl)phenols

Hiroyuki Konno* , Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan; Fax + 81-22-217-6845; E-mail: konol@mail.cc.tohoku.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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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