Stereoselective trimerization of [(S)R]-[(p-tolylsulfinyl)methyl]-p-quinols and p-quinamines

Org Lett. 2003 Jul 10;5(14):2425-8. doi: 10.1021/ol034589t.

Abstract

[reaction: see text] The asymmetric synthesis of pentacyclic derivatives was achieved in a single step starting from enantiopure [(S)R]-[(p-tolylsulfinyl)methyl]-p-quinols or the nitrogen analogue, through a domino sequence involving four conjugate additions in excellent yields. Eight new stereogenic centers were created in one step and in a highly diastereoselective manner.