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

LETTER

Application of a Double Mannich Reaction Using Bis(aminol) Ethers in the Synthesis of AE Ring Analogues of Methyl Lycaconitine

Constanze Brocke^a, Margaret A. Brimble*^a, Diana S.-H. Lin^b, Malcolm D. McLeod^b
^a Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;
^b School of Chemistry, F11, University of Sydney, Camperdown, NSW 2006, Australia

Abstract

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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.

Key words

Mannich reaction - aminoalkylation - bis(aminol) ethers - methyl lycaconitine - alkaloids

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References

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