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

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

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

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

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 language	English
Pages (from-to)	1559-1560
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	13
Publication status	Published - 1994

Cite this

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

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.",

author = "Bailey, \{P. D.\} and Collier, \{I. D.\} and Hollinshead, \{S. P.\} and Moore, \{M. H.\} and Morgan, \{K. M.\} and Smith, \{D. I.\} and Vernon, \{J. M.\}",

year = "1994",

language = "English",

pages = "1559--1560",

journal = "Journal of the Chemical Society, Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "13",

}

TY - JOUR

T1 - A new asymmetric route to bridged indole alkaloids

T2 - Formal syntheses of (-)-suaveoline, (-)-raumacline and (-)-Nb-methylraumacline

AU - Bailey, P. D.

AU - Collier, I. D.

AU - Hollinshead, S. P.

AU - Moore, M. H.

AU - Morgan, K. M.

AU - Smith, D. I.

AU - Vernon, J. M.

PY - 1994

Y1 - 1994

N2 - 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.

AB - 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.

M3 - Article

SN - 0022-4936

SP - 1559

EP - 1560

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 13

ER -

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

Abstract

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