Application of a double Mannich reaction using bis(aminol) ethers in the synthesis of AE ring analogues of methyl lycaconitine

Constanze Brocke; Margaret A. Brimble; Diana S.H. Lin; Malcolm D. McLeod

doi:10.1055/s-2004-831340

Application of a double Mannich reaction using bis(aminol) ethers in the synthesis of AE ring analogues of methyl lycaconitine

Constanze Brocke, Margaret A. Brimble^*, Diana S.H. Lin, Malcolm D. McLeod

^*Corresponding author for this work

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

23 Citations (Scopus)

Abstract

An efficient method for the construction of azabicyclo[3.3.1]nonanes and azabicyclo[3.2.1]octanes is reported via double Mannich reaction of cyclic ketoesters with bis(aminol) ethers. This method is applied to the synthesis of AE ring analogues of methyl lycaconitine.

Original language	English
Pages (from-to)	2359-2363
Number of pages	5
Journal	Synlett
Issue number	13
DOIs	https://doi.org/10.1055/s-2004-831340
Publication status	Published - 3 Nov 2004
Externally published	Yes

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title = "Application of a double Mannich reaction using bis(aminol) ethers in the synthesis of AE ring analogues of methyl lycaconitine",

abstract = "An efficient method for the construction of azabicyclo[3.3.1]nonanes and azabicyclo[3.2.1]octanes is reported via double Mannich reaction of cyclic ketoesters with bis(aminol) ethers. This method is applied to the synthesis of AE ring analogues of methyl lycaconitine.",

keywords = "Alkaloids, Aminoalkylation, Mannich reaction, Methyl lycaconitine, bis(aminol) ethers",

author = "Constanze Brocke and Brimble, {Margaret A.} and Lin, {Diana S.H.} and McLeod, {Malcolm D.}",

year = "2004",

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T1 - Application of a double Mannich reaction using bis(aminol) ethers in the synthesis of AE ring analogues of methyl lycaconitine

AU - Brocke, Constanze

AU - Brimble, Margaret A.

AU - Lin, Diana S.H.

AU - McLeod, Malcolm D.

PY - 2004/11/3

Y1 - 2004/11/3

N2 - An efficient method for the construction of azabicyclo[3.3.1]nonanes and azabicyclo[3.2.1]octanes is reported via double Mannich reaction of cyclic ketoesters with bis(aminol) ethers. This method is applied to the synthesis of AE ring analogues of methyl lycaconitine.

AB - An efficient method for the construction of azabicyclo[3.3.1]nonanes and azabicyclo[3.2.1]octanes is reported via double Mannich reaction of cyclic ketoesters with bis(aminol) ethers. This method is applied to the synthesis of AE ring analogues of methyl lycaconitine.

KW - Alkaloids

KW - Aminoalkylation

KW - Mannich reaction

KW - Methyl lycaconitine

KW - bis(aminol) ethers

UR - http://www.scopus.com/inward/record.url?scp=8644284908&partnerID=8YFLogxK

U2 - 10.1055/s-2004-831340

DO - 10.1055/s-2004-831340

M3 - Article

SN - 0936-5214

SP - 2359

EP - 2363

JO - Synlett

JF - Synlett

IS - 13

ER -

Application of a double Mannich reaction using bis(aminol) ethers in the synthesis of AE ring analogues of methyl lycaconitine

Abstract

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