Optically active trans - and cis -ring junction decalinic intermediates, which represent useful precursors for the synthesis of more complex natural targets, have been conveniently prepared starting from the β-ketoester obtained by standard chemistry from β-ionone and dimethyl carbonate. The chiral auxiliary (−)-menthol, easily attached to the β-ketoester through DMAP-catalyzed transesterification, allowed a clean separation of the diastereomers obtained in the key electrocyclization step, which were further elaborated to chiral intermediates already taken to drimane and labdane sesquiterpenes.

An efficient approach to chiral nonracemic trans- and cis-decalin scaffolds for drimane and labdane synthesis

POLLINI, Gian Piero;BIANCHI, Anna;CASOLARI, Alberto;DE RISI, Carmela;ZANIRATO, Vinicio;BERTOLASI, Valerio
2004

Abstract

Optically active trans - and cis -ring junction decalinic intermediates, which represent useful precursors for the synthesis of more complex natural targets, have been conveniently prepared starting from the β-ketoester obtained by standard chemistry from β-ionone and dimethyl carbonate. The chiral auxiliary (−)-menthol, easily attached to the β-ketoester through DMAP-catalyzed transesterification, allowed a clean separation of the diastereomers obtained in the key electrocyclization step, which were further elaborated to chiral intermediates already taken to drimane and labdane sesquiterpenes.
2004
Pollini, Gian Piero; Bianchi, Anna; Casolari, Alberto; DE RISI, Carmela; Zanirato, Vinicio; Bertolasi, Valerio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1198113
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