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Synthesis 2012(3): 469-473  
DOI: 10.1055/s-0031-1289643
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

First Stereoselective Total Synthesis of Naturally Occurring (6R)-6-(4-Oxopentyl)-5,6-dihydro-2H-pyran-2-one and Its (6S)-Enantiomer [¹]

Digambar Balaji Shinde, Boddu Shashi Kanth, Malampati Srilatha, Biswanath Das*
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500607, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.com;
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Publication History

Received 10 October 2011
Publication Date:
15 December 2011 (online)

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Abstract

(6R)-6-(4-Oxopentyl)-5,6-dihydro-2H-pyran-2-one, a naturally occurring α,β-unsaturated δ-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.

Key words

lactones - (6R)-6-(4-oxopent-2-enyl)-5,6-dihydro-2H-pyran-2-one - (6S)-6-(4-oxopent-2-enyl)-5,6-dihydro-2H-pyran-2-one - ring-closing metathesis - stereoselective synthesis

1

Part 52 in the series, ‘Synthetic Studies on Natural Products’.

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1

Part 52 in the series, ‘Synthetic Studies on Natural Products’.