Non-natural elemane as the "stepping stone" for the synthesis of germacrane and guaiane sesquiterpenes.

Elissavet E Anagnostaki, Alexandros L Zografos

Index: Org. Lett. 15(1) , 152-5, (2013)

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Abstract

The synthesis of hydroxyelemane 5 from (R)-carvone and its utilization as a common synthetic scaffold to produce structurally diverse germacrane and guaiane sesquiterpenes are described. A highly enantio- and stereoselective biomimetic tandem oxy-Cope/ene rearrangement was used as the key reaction to access the 10-membered macrocyclic core of germacranes and the condensed 5-7 carbocycles of guaiane sesquiterpenes. Additionally, reactions of furanoguaianes under acidic or oxidizing reagents have been investigated, and preliminary results of these conversions are presented.