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Synlett 2000; 2000(6): 0890-0892
DOI: 10.1055/s-2000-6698
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Bisabolane Sesquiterpenes: Synthesis of (R)-(+)-Sydowic Acid and (R)-(+)-Curcumene Ether

Stefano Serra*
  • *Dip. di Chimica del Politecnico, Centro CNR per la Chimica delle Sostanze Organiche Naturali, Via Mancinelli 7, 20131 Milano, Italy; Fax 39 2 23993080; E-mail: lab545@dept.chem.polimi.it
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Publication Date:
31 December 2000 (online)

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A stereoselective synthesis of (R)-(+)-sydowic acid 1 and (R)-(+)-curcumene ether 2 is described. The enantiomerically pure tetrahydropyran building block (R)-(-)-cinenic acid 5 is obtained by resolution of the racemic acid. The aromatic moiety is constructed using a benzoannulation reaction as a key step. An easy way to the title compounds in racemic form is also reported.

annulations - cyclizations - sesquiterpenes - tetrahydropyran - phenols