Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

作者：Davies Stephen G^*; Fletcher Ai M; Roberts Paul M; Smith Andrew D

来源：Tetrahedron, 2009, 65(49): 10192-10213.

DOI：10.1016/j.tet.2009.09.104

• Lithium amides
• Asymmetric synthesis
• Ring-closing metathesis
• Sedum alkaloids
• Sedamine

Conjugate addition of lithium (R)-N-allyl-N-(alpha-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(alpha-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 P-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.

• 出版日期2009-12-5