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Synfacts 2007(1): 0005-0005
DOI: 10.1055/s-2006-955645
DOI: 10.1055/s-2006-955645
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Valilactone
Y. Wu*, Y.-P. Sun
Shanghai Institute of Organic Chemistry, P. R. of China
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
15. Dezember 2006 (online)
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.