Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Journal article

Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues. © 2009 Elsevier Ltd. All rights reserved.

Authors: Davies, S; Fletcher, A; Roberts, P; Smith, A

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 65
• Issue: 49
• Pages: 10192-10213
• Publication date: 2009-12-05
• DOI: 10.1016/j.tet.2009.09.104
• ISSN: 0040-4020
• Language: English
• Keywords: Asymmetric synthesis; Sedum alkaloids; Lithium amides; Ring-closing metathesis; Sedamine