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Synthesis 2011(12): 1954-1959  
DOI: 10.1055/s-0030-1260051
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Enantioselective Approach to the Synthesis of Verbalactone and (R)-Massoialactone

Anand Harbindu, Pradeep Kumar*
Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India
Fax: +91(20)25902629; e-Mail: pk.tripathi@ncl.res.in;
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Publication History

Received 15 March 2011
Publication Date:
17 May 2011 (online)

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Abstract

The organocatalytic enantioselective synthesis of verbalactone and (R)-massoialactone is described. The requisite stereogenic centers of the target molecules were constructed using l-proline-catalyzed α-aminoxylation and Horner-Wadsworth-Emmons­ (HWE) olefination. Yamaguchi macrolactonization and ring-closing metathesis were employed as key steps in the syntheses.

Key words

l-proline - α-aminoxylation - Horner-Wadsworth-Emmons­ olefination - Yamaguchi macrolactonization - ring-closing metathesis - verbalactone - massoialactone

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The enantiomeric excess(ee) of 7 was determined by derivatizing its precursor α,β-unsaturated γ-hydroxy ester with Mosher’s acid and analyzing the ¹9F NMR spectrum. The ee was found to be >97%.