112763-97-0Relevant articles and documents
Stereoselective synthesis of (-)-tetrahydrolipstatin via a radical cyclization based strategy
Yadav,Vishweshwar Rao,Sridhar Reddy,Prasad
, p. 4393 - 4395 (2007/10/03)
An efficient and flexible approach for the total synthesis of (-)-tetrahydrolipstatin is described. The main features of the synthetic strategy are a stereocontrolled radical cyclization and the successful utilization of commercially available S-malic acid.
Total synthesis of (-)-tetrahydrolipstatin
Hanessian,Tehim,Chen
, p. 7768 - 7781 (2007/10/02)
The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain- extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91% ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38% overall yield.
Stereoselective syntheses of tetrahydrolipstatin and of an analogue, potent pancreatic-lipase inhibitors containing a β-lactone moiety
Barbier,Schneider,Widmer
, p. 1412 - 1418 (2007/10/02)
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