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Synthesis 2010(21): 3627-3630  
DOI: 10.1055/s-0030-1258248
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of (-)-6-Acetoxy-5-hexadecanolide by Organocatalytic α-Oxygenation-Allylation-RCM Strategy

Youngju Park, Jinsung Tae*
Department of Chemistry and Center for Bioactive Molecular Hybrids (CBMH), Yonsei University, Seoul 120-749, Korea
Fax: +82(2)3647050; e-Mail: jstae@yonsei.ac.kr;
Further Information

Publication History

Received 9 July 2010
Publication Date:
07 September 2010 (online)

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Abstract

An asymmetric total synthesis of (-)-6-acetoxy-5-hexadecanolide has been accomplished by employing a seven-step sequence. Asymmetric α-benzoyloxylation of dodecanal followed by indium-mediated one-pot allylation produces the anti-1,2-diol. The six-membered lactone ring is constructed by RCM reaction.

Key words

allylation - α-benzoyloxylation - metathesis - organocatalysts - total synthesis

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At this point, the minor diastereomer is separated by column chromatography in 15% yield.