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Synthesis 2015; 47(15): 2299-2316
DOI: 10.1055/s-0034-1380215
DOI: 10.1055/s-0034-1380215
paper
Stereoselective Total Synthesis of the Diastereomeric Tricyclic Alkaloids Tetraponerine-7 and Tetraponerine-8 Using O-Pivaloylated d-Arabinopyranosylamine as the Common Auxiliary
Further Information
Publication History
Received: 23 March 2015
Accepted after revision: 21 April 2015
Publication Date:
11 June 2015 (online)
Dedicated to Professor Richard R. Schmidt on the occasion of his 80th birthday
Abstract
Based on a diastereoselective domino Mannich–Michael reaction cascade of 2-N-[(S)-3-{(benzyloxycarbonyl)[4-(tert-butyldiphenylsiloxy)butyl]amino}octylidene]-2,3,4-tri-O-pivaloyl-α-d-arabinopyranosylamine with the Danishefsky diene, the major component of the neurotoxic venom of the New Guinean ant Tetraponera punctulata, tetraponerine-8, and its diastereomer tetraponerine-7 were synthesized in pure form. While the Mannich reaction of the arabinosyl imine of the required (S)-configured β-aminoaldehyde gave the 2-substituted piperidinone precursor of tetraponerine-8 with excellent diastereoselectivity, the analogous Mannich reaction of the (R)-configured β-aminoaldehyde afforded the precursor of tetraponerine-7 with a selectivity of only 2:1 (mismatched case). The enantiomerically pure tetraponerine-8, described as highly toxic for ants, exhibited only moderate toxicity to sucking and stinging insects.
Key words
piperidine alkaloids - tetraponerines - stereoselective Mannich–Michael reaction - carbohydrate auxiliaries - nicotinic acetylcholine receptor inhibitorSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380215.
- Supporting Information
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