Asymmetric Synthesis of (-)-Lentiginosine by Double Aza-Michael Reaction

作者：Liu Sin Wei; Hsu He Chu; Chang Chiao Hsin; Tsai Hui Hsu Gavin; Hou Duen Ren^*

来源：European Journal of Organic Chemistry, 2010, 2010(25): 4771-4773.

DOI：10.1002/ejoc.201000691

• Aza-Michael reaction
• Alkaloids
• Asymmetric synthesis
• Metathesis

Total synthesis of (-)-lentiginosine (1) was achieved in nine steps from (3R, 4R)-3,4-dihydroxy-1,5-hexadiene (2). Cross metathesis, vinyl addition and DDQ oxidation were applied to generate the key 3-oxonona-1,4,8-triene 6, which was cyclised to 4-oxopiperidine 7 by diastereoselective double aza-Michael reaction. Both theoretical and empirical studies support that the stereochemical assignment of the major Michael adduct is the desired (2R)-4-oxopiperidine 7.

• 出版日期2010-9
• 单位中央民族大学