| Title : Total synthesis and comparative analysis of orlistat, valilactone, and a transposed orlistat derivative: Inhibitors of fatty acid synthase - Ma_2006_Org.Lett_8_4497 |
| Author(s) : Ma G , Zancanella M , Oyola Y , Richardson RD , Smith JW , Romo D |
| Ref : Org Lett , 8 :4497 , 2006 |
|
Abstract :
Concise syntheses of orlistat (Xenical), a two-carbon transposed orlistat derivative, and valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the alpha-side chain. Versatile strategies for modifying the delta-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling. |
| PubMedSearch : Ma_2006_Org.Lett_8_4497 |
| PubMedID: 16986934 |
| Inhibitor | Valilactone |
Ma G, Zancanella M, Oyola Y, Richardson RD, Smith JW, Romo D (2006)
Total synthesis and comparative analysis of orlistat, valilactone, and a transposed orlistat derivative: Inhibitors of fatty acid synthase
Org Lett
8 :4497
Ma G, Zancanella M, Oyola Y, Richardson RD, Smith JW, Romo D (2006)
Org Lett
8 :4497