Unusual biomimetic oxidations of indoles: Synthesis of suaveoline and an alkaloid G analogue

Patrick D. Bailey; Keith M. Morgan; Georgina M. Rosair; Rhodri L. Thomas

doi:10.1016/S0040-4039(99)01684-6

Unusual biomimetic oxidations of indoles: Synthesis of suaveoline and an alkaloid G analogue

Patrick D. Bailey, Keith M. Morgan, Georgina M. Rosair, Rhodri L. Thomas

School of Engineering & Physical Sciences

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

10 Citations (Scopus)

Abstract

The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a synthesis of suaveoline can be oxidatively cyclized to 16.

Original language	English
Pages (from-to)	8255-8259
Number of pages	5
Journal	Tetrahedron Letters
Volume	40
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(99)01684-6
Publication status	Published - 19 Nov 1999

Keywords

Alkaloids
Indoles
Oxidation

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10.1016/S0040-4039(99)01684-6

Cite this

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title = "Unusual biomimetic oxidations of indoles: Synthesis of suaveoline and an alkaloid G analogue",

abstract = "The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a synthesis of suaveoline can be oxidatively cyclized to 16.",

keywords = "Alkaloids, Indoles, Oxidation",

author = "Bailey, \{Patrick D.\} and Morgan, \{Keith M.\} and Rosair, \{Georgina M.\} and Thomas, \{Rhodri L.\}",

year = "1999",

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T1 - Unusual biomimetic oxidations of indoles

T2 - Synthesis of suaveoline and an alkaloid G analogue

AU - Bailey, Patrick D.

AU - Morgan, Keith M.

AU - Rosair, Georgina M.

AU - Thomas, Rhodri L.

PY - 1999/11/19

Y1 - 1999/11/19

N2 - The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a synthesis of suaveoline can be oxidatively cyclized to 16.

AB - The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a synthesis of suaveoline can be oxidatively cyclized to 16.

KW - Alkaloids

KW - Indoles

KW - Oxidation

UR - https://www.scopus.com/pages/publications/0033584942

U2 - 10.1016/S0040-4039(99)01684-6

DO - 10.1016/S0040-4039(99)01684-6

M3 - Article

VL - 40

SP - 8255

EP - 8259

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Unusual biomimetic oxidations of indoles: Synthesis of suaveoline and an alkaloid G analogue

Abstract

Keywords

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