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Synfacts 2010(1): 0006-0006
DOI: 10.1055/s-0029-1218402
DOI: 10.1055/s-0029-1218402
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (-)-Tetrahydrolipstatin
A. K. Ghosh*, K. Shurrush, S. Kulkarni
Purdue University, West Lafayette, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Dezember 2009 (online)
Significance
(-)-Tetrahydrolipstatin is used for the treatment of obesity under the trade name Orlistat. It inhibits gastric and pancreatic lipases resulting in slow hydrolysis of triglycerides into free fatty acids. It is also known as a potent inhibitor of fatty acid synthase, an enzyme responsible for fatty acid synthesis in many human carcinomas. The pivotal anti-aldol segment I is synthesized via a nonaldol route involving a Lewis acid catalyzed diastereoselective ring opening of THF F to afford styrene derivative G as a key step.