NEW ASYMMETRIC ROUTE TO BRIDGED INDOLE ALKALOIDS - FORMAL SYNTHESES OF (-)-SUAVEOLINE, (-)-RAUMACLINE AND (-)-N-B-METHYLRAUMACLINE

Authors
BAILEY PD COLLIER ID HOLLINSHEAD SP MOORE MH MORGAN KM SMITH DI VERNON JM
Citation
Pd. Bailey et al., NEW ASYMMETRIC ROUTE TO BRIDGED INDOLE ALKALOIDS - FORMAL SYNTHESES OF (-)-SUAVEOLINE, (-)-RAUMACLINE AND (-)-N-B-METHYLRAUMACLINE, Journal of the Chemical Society, Chemical Communications, (13), 1994, pp. 1559-1560
Citations number
14
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
13
Year of publication
1994
Pages
1559 - 1560
Database
ISI
SICI code
0022-4936(1994):13<1559:NARTBI>2.0.ZU;2-T
Abstract
When the homologated nitrile 11 derived from L-tryptophan undergoes a modified Pictet-Spengler reaction with methyl propynoate, the resultin g cis-tetrahydro-beta-carboline 12a is ideally functionalised for cycl isation to the bridged ketonitrile 14; simple functional group modific ations via the nitrile 15 (structure confirmed by X-ray crystallograph y) allow convergence with the tetracyclic alpha,beta-unsaturated aldeh yde 10, which is an advanced intermediate for the synthesis of a range of bridged indole alkaloids.