Miho Saito, J. Matsuo, H. Ishibashi*
Jun 4, 2007
Citations
0
Influential Citations
10
Citations
Journal
Tetrahedron
Abstract
Abstract Treatment of N -(2-arylcyclohex-1-en-1-yl)-α-(methylthio)acetamides with N -chlorosuccinimide (NCS) gave 3a-aryl-2,3,3a,4,5,6-hexahydro-3-(methylthio)indol-2-ones. Desulfurization of the cyclization products followed by a catalytic hydrogenation of the resulting hexahydroindol-2-ones gave predominantly or exclusively trans-fused octahydroindol-2-ones. On the other hand, reduction of the desulfurization products with Et 3 SiH in CF 3 CO 2 H exclusively provided cis-fused octahydroindol-2-ones. A chiral induction of N -[2-(3,4-dimethoxy)phenylcyclohex-1-en-1-yl]-α-(methylthio)acetamide having an ( R )-1-(1-naphthyl)ethyl group on the nitrogen atom led to the synthesis of (−)-mesembrane and (−)- trans -mesembrane.