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Synfacts 2007(1): 0005-0005  
DOI: 10.1055/s-2006-955645
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Valilactone

Contributor(s): Philip Kocienski
Y. Wu*, Y.-P. Sun
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

Valilactone inhibits pancreatic lipase about 103 times more effectively than tetra­hydrolipstatin, a related β-lactone marketed as Xenical or Orlistat for the treatment of obesity. The key steps in the synthesis depicted were (a) a Crimmins directed aldol reaction to form C and (b) a hydroxyl-directed diastereoselective reduction of D.