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Merck

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

Organic letters (2012-12-22)
Elissavet E Anagnostaki, Alexandros L Zografos
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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.

MATERIALS
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Sigma-Aldrich
L-Carvone, natural, 99%, FG
Sigma-Aldrich
L-Carvone, โ‰ฅ97%, FCC, FG
Supelco
(+)-Carvone, certified reference material, TraceCERTยฎ, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
(S)-(+)-Carvone, 96%
Sigma-Aldrich
(R)-(โˆ’)-Carvone, 98%
Supelco
(โˆ’)-Carvone, analytical standard
Sigma-Aldrich
D-Carvone, โ‰ฅ96%, FG
Supelco
(+)-Carvone, analytical standard