An efficient synthesis of pterosin C and other pterosins

Autor:	Kam-Mui Eva Ng, Trevor C. McMorris
Rok vydání:	1984
Předmět:	chemistry.chemical_classification Ketone Bicyclic molecule Stereochemistry Organic Chemistry Diol General Chemistry Sesquiterpene Catalysis Acylation chemistry.chemical_compound chemistry Acyl chloride Organic chemistry Demethylation
Zdroj:	Canadian Journal of Chemistry. 62:1945-1953
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v84-334
Popis:	A versatile synthetic route to pterosins, sesquiterpenoid indanones present in bracken, Pteridiumaquilinum, has been developed. The route is exemplified by the synthesis of (2S,3S)-pterosin C by Friedel–Crafts bisacylation of the methyl ether of 2-(2,6-dimethylphenyl)ethanol with methylmalonyl chloride. Demethylation of the resulting 1,3-indandione and reduction with zinc and acetic acid in the presence of acetic anhydride and sodium acetate afforded a mixture of racemic cis and trans isomers of pterosin C diacetate, which was hydrolysed to the corresponding pterosins. Separation and resolution via the S-(+)-α-phenylbutyric esters gave (2S,3S)-pterosin C and (2R,3R)-pterosin C. Other pterosins were prepared as racemates from the 1,3-indandione.
Databáze:	OpenAIRE
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