Syntheses of 3-O-Demethylthalicthuberine and N-Acetyl-seco-N-methyllaurotetanine

Syntheses of 3-O-Demethylthalicthuberine and N-Acetyl-seco-N-methyllaurotetanine

The structures previously assigned to the phenanthrene alkaloids 3-O-demethylthalicthuberine and N-acetyl-seco-N methyllaurotetanine have been confirmed by total syntheses in which the key step involved formation of ring C of the aporphine alkaloids (±)-isodomesticine and O-benzyl-N-methyllaurotetan...

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Bibliographic Details
Main Authors: Rujee Lorpitthaya, Surachai Nimgirawath, Jumrern Laosriratana
Format: Article
Language:English
Published: Prince of Songkla University 2006-11-01
Series:Songklanakarin Journal of Science and Technology (SJST)
Subjects:
alkaloid
aporphine
phenanthrene
synthesis
radical cyclization
Online Access:http://www.sjst.psu.ac.th/journal/28_6_pdf/08-alkaloid.pdf
Description
Summary:The structures previously assigned to the phenanthrene alkaloids 3-O-demethylthalicthuberine and N-acetyl-seco-N methyllaurotetanine have been confirmed by total syntheses in which the key step involved formation of ring C of the aporphine alkaloids (±)-isodomesticine and O-benzyl-N-methyllaurotetanine by a radical-initiated cyclization. Opening of ring B of (±) isodomesticine with methyl chloroformate and subsequent reduction of the N-carbomethoxy group afforded 3-O demethylthalicthuberine. Similarly, ring-B opening of N-methyllaurotetanine with acetyl bromide followed by hydrolysis afforded N-acetyl-seco-Nmethyllaurotetanine.
ISSN:0125-3395

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