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Syntheses of (−)-Cryptocaryolone and (−)-Cryptocaryolone Diacetate via a Diastereoselective Oxy-Michael Addition and Oxocarbenium Allylation

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journal contribution
posted on 17.08.2012, 00:00 by Aymara M. M. Albury, Michael P. Jennings
The total syntheses of both (−)-cryptocaryolone and (−)-cryptocaryolone diacetate is presented herein. The usage of a diastereoselective oxy-Michael addition/benzylidene acetal formation coupled with a selective axial oxocarbenium allylation allowed for the preparation of the α-C-glycoside moiety present in the bicyclic bridged structure. In addition, the syn-1,3-diol of the linear portion was installed via a Wacker oxidation followed by a subsequent directed reduction of the appropriate homoallylic alcohol precursor.