Article

Enantioselective, biocatalytic reduction of 3-substituted cyclopentenones: application to the asymmetric synthesis of an hNK-1 receptor antagonist.

Department of Process Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, USA.
Organic Letters (impact factor: 5.86). 02/2011; 13(5):1004-7. DOI:10.1021/ol1030348 pp.1004-7
Source: PubMed

ABSTRACT A convergent and enantioselective route to the hNK-1 receptor antagonist (1) is described, which sets all six stereogenic centers with high diastereoselectivity and delivers 1 in only 11 steps and 23% overall yield. The process was enabled by the development of the enantioselective enzymatic reduction of 3-functionalized cyclopentenones and stereospecific Pd-catalyzed etherification coupling of fragments 6 and 7.

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Keywords

3-functionalized cyclopentenones
 
diastereoselectivity
 
enantioselective enzymatic reduction
 
six stereogenic centers
 
stereospecific Pd-catalyzed etherification coupling
 

Kevin R Campos