FIELD: chemistry.
SUBSTANCE: in first step of synthesis of betulinic acid (1) from betulin, the primary C28-hydroxyl is protected using a vinyl group which is incorporated via selective C28-O-vinylation of betulin with acetylene in a super-basic DMSO-KOH medium. Subsequent C3-O-acetylation of 28-O-vinyl ester of betulin and treatment of 3β-acetoxy-28-O-vinyl ester of betulin without extracting concentrated HCl from the reaction mass yields 3β-acetoxybetulin, whose two-step oxidation into a corresponding aldehyde, then into an acid and via hydrolysis of 3β-acetoxybetulinic acid yields the desired acid (1).
EFFECT: method cuts time, financial and labour costs when producing the acid and increases output.
1 ex
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Authors
Dates
2015-10-20—Published
2014-10-20—Filed