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First Stereoselective Total Synthesis of Naturally Occurring (6R)-6-(4-Oxopentyl)-5,6-dihydro-2H-pyran-2-one and Its (6S)-Enantiomer
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First Stereoselective Total Synthesis of Naturally Occurring (6R)-6-(4-Oxopentyl)-5,6-dihydro-2H-pyran-2-one and Its (6S)-Enantiomer

Digambar Balaji Shinde, Boddu Shashi Kanth, Malampati Srilatha and Biswanath Das
Synthesis (Stuttgart), Vol.44(3), pp.469-473
01/02/2012

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
(6R)-6-(4-Oxopentyl)-5,6-dihydro-2H-pyran-2-one, a naturally occurring alpha,beta-unsaturated delta-lactone, and its (6S)-enantiomer have been synthesized stereoselectively starting from pentane-1,5-diol. The synthesis involves Maruoka asymmetric allylation and ring-closing metathesis as the key steps.

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