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Synthesis 2011(12): 1954-1959
DOI: 10.1055/s-0030-1260051
DOI: 10.1055/s-0030-1260051
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Organocatalytic Enantioselective Approach to the Synthesis of Verbalactone and (R)-Massoialactone
Further Information
Received
15 March 2011
Publication Date:
17 May 2011 (online)
Publication History
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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References
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%.