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

DOI: 10.1039/c39940001559

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 1559 - 1560 (1994)

Update date:2022-08-04

Topics:

Authors:

Bailey Bailey

Collier Collier

Hollinshead

Moore Moore

Morgan Morgan

Smith Smith

Vernon Vernon

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Article abstract of DOI:10.1039/c39940001559

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 modifications 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.

Full text of DOI:10.1039/c39940001559

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