A novel domino (4+2)/(4+2)/(3+2) cycloaddition reaction leading to highly functionalized polycyclic nitroso acetals
van Berkom LWA, Kuster GJT, Kalmoua F, de Gelder R, Scheeren HW
TETRAHEDRON LETTERS
44 (27): 5091-5093 JUN 30 2003


Abstract:
2-Methoxybuta-1,3-diene reacts under high pressure conditions in a one-pot domino (4+2)/(4+2)/(3+2) cycloaddition reaction with a dienophile, beta-nitrostyrene and a dipolarophile to give tri, tetra and pentacyclic nitroso acetals. In this novel domino reaction up to six bonds and up to eight stereogenic centers are created in one step in good yield and good stereoselectivity.