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A concise and stereoselective synthesis of both enantiomers of altholactone and isoaltholactone

✍ Scribed by J.S. Yadav; G. Rajaiah; A.Krishnam Raju

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
236 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A concise and flexible stereoselective route to synthesize both enantiomers of the highly functionalized a,b-unsaturatedd-lactones, altholactone and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulphonic acid.

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