A new asymmetric route to bridged indole alkaloids: formal syntheses of (–)-suaveoline, (–)-raumacline and (–)-Nb-methylraumacline

Autor: Madeleine H. Moore, John M. Vernon, Keith M. Morgan, Patrick D. Bailey, Ian D. Collier, David I. Smith, S. P. Hollinshead
Rok vydání: 1994
Předmět:
Zdroj: J. Chem. Soc., Chem. Commun.. :1559-1560
ISSN: 0022-4936
DOI: 10.1039/c39940001559
Popis: When the homologated nitrile 11 derived from L-tryptophan undergoes a modified Pictet–Spengler reaction with methyl propynoate, the resulting cis-tetrahydro-β-carboline 12a is ideally functionalised for cyclisation to the bridged ketonitrile 14; simple functional group modification via the nitrile 15(structure confirmed by X-ray crystallography) allow convergence with the tetracyclic α,β-unsaturated aldehyde 10, which is an advanced intermediate for the synthesis of a range of bridged indole alkaloids.
Databáze: OpenAIRE