Synthesis of (3'R, 5'S)-3'-hydroxycotinine using 1,3-dipolar cycloaddition of a nitrone

Abstract To synthesize (3′ R ,5′ S )-3′-hydroxycotinine [ (+)- 1 ], the main metabolite of nicotine ( 2 ), cycloaddition of C -(3-pyridyl)nitrones 3a , 3c , and 15 with (2 R )- and (2 S )- N -(acryloyl)bornane-10,2-sultam [(2 R )- and (2 S )- 8 ] was examined. Among them, l -gulose-derived nitrone 15 underwent stereoselective cycloaddition with (2 S )- 8 to afford cycloadduct 16 , which was elaborated to (+)- 1 .