ISSN:
0947-3440
Keywords:
Total synthesis of (+)-3-Oxacarbacyclin
;
Stereoselective deprotonation
;
Chiral lithium amide
;
Prostaglandins
;
Asymmetric synthesis
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The asymmetric synthesis of (+)-3-oxacarbacyclin (1) from cis-bicyclo[3.3.0]octane-2,5-dione has been achieved. A notable feature in this synthesis is an asymmetric Horner-Wadsworth-Emmons (HWE) reaction. A further key step is the stereoselective deprotonation of a chiral bicyclic ketone, having a high local symmetry about the carbonyl group, with lithium (R,R)-bis(phenylethyl)amide in the presence of lithium chloride. The route described also allows the synthesis of the anti-thrombotic and anti-metastatic prostacyclin analogs cicaprost and eptaloprost. The flexibility of this route should also provide access to further side-chain modified analogs of 1.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719971206
