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

P. D. Bailey, I. D. Collier, S. P. Hollinshead, M. H. Moore, K. M. Morgan, D. I. Smith, J. M. Vernon

Research output: Contribution to journalArticlepeer-review

Abstract

When the homologated nitrile 11 derived from L-tryptophan undergoes a modified Pictet-Spengler reaction with methyl propynoate, the resulting cis-tetrahydro-ß-carboline 12a is ideally functionalised for cyclisation to the bridged ketonitrile 14; simple functional group modifications via the nitrile 15 (structure confirmed by X-ray crystallography) allow convergence with the tetracyclic a,ß-unsaturated aldehyde 10, which is an advanced intermediate for the synthesis of a range of bridged indole alkaloids.

Original languageEnglish
Pages (from-to)1559-1560
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number13
Publication statusPublished - 1994

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