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Partial synthesis of 6β-sesquiterpenolides from 6α-sesquiterpenolides

✍ Scribed by José L. Bretón; Juan J. Cejudo; Andrés García-Granados; Andrés Parra; Francisco Rivas

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
206 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

AlSSTRAm

Chemikai means were used to achieve the epimetimtion at C-4 of bu-eudesmanolides, with several ji4n&na&zations, to @udesmanolides.

The process consists of the L.iAlH4 reduction of a 6a-iactone, selective acetyW of the hydmxymethyiene group at C-12 midclton and rerluction at C-4 to epimerize this ca&on., ahcetykztion at C-12 and final fomuztion of a 6J-lactone with RuHz(PhSp)+ The whole pmcess yielab near& 40%

of the 6@4actone, ox&don with the nrthenium reagent (58 and 53%) being the limiting step.

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