Use of the electrophilic arylation reaction of aryl-lead triacetates in a synthesis of (±)-lycoramine
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 2695-2700
- https://doi.org/10.1039/p19870002695
Abstract
A formal total synthesis of (±)-lycoramine is reported. The quaternary carbon centre of the alkaloid was produced by a novel electrophilic arylation of the mixture of isomeric vinylogous keto esters (4) and (5) by 2,3-dimethoxyphenyl-lead triacetate. The resulting key intermediate (7c), which was formed in almost quantitative yield, was converted in a straightforward sequence into the formamide (25), from which the alkaloid has been produced previously by a Bischler-Napieralski cyclisation. Functional group protection was only required at one stage in the synthesis.This publication has 4 references indexed in Scilit:
- Use of the electrophilic arylation reaction of aryl-lead triacetates in a synthesis of (±)-lycoramineJournal of the Chemical Society, Perkin Transactions 1, 1987
- Total synthesis of racemic lycoramineThe Journal of Organic Chemistry, 1984
- General methods for alkaloid synthesis. Total synthesis of racemic lycoramineThe Journal of Organic Chemistry, 1982
- Vesicant principles of Poison Ivy and related plants: synthesis of the urushiols, 1,2- dihydroxy-3-[(Z)-pentadec-8-enyl]benzene and 1,2 dihydroxy-3-pentadecylbenzeneJournal of the Chemical Society, Perkin Transactions 1, 1980