Total synthesis of (-)-senepodine G and (-)-cermizine C.
An efficient, stereospecific synthesis of the alkaloids senepodine G (2) and cermizine C (1) has been completed using the BF3.Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3, the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).
Snider
Barry B
BB
Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
Grabowski
James F
JF
D000470:Alkaloids / Q000138:chemical synthesis*; D001880:Boranes / Q000737:chemistry; D001894:Borohydrides / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D007769:Lactams / Q000737:chemistry; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000470:Alkaloids; D001880:Boranes; D001894:Borohydrides; D006574:Heterocyclic Compounds, 2-Ring; D007769:Lactams; D009942:Organometallic Compounds; C518697:cermizine C; C518698:senepodine G; C021274:boron trifluoride; C025364:sodium borohydride