Stereoselective One-Step Construction of Vicinal Quaternary and Tertiary Stereocenters of the 5, 10b-Ethanophenanthridine Skeleton: Total Synthesis of (±)-Maritidine

G Pandey, NR Gupta, TM Pimpalpalle

Index: Pandey, Ganesh; Gupta, Nishant R.; Pimpalpalle, Tukaram M. Organic Letters, 2009 , vol. 11, # 12 p. 2547 - 2550

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Citation Number: 22

Abstract

The challenging vicinal quaternary and tertiary stereocenters of the 5, 10b- ethanophenanthridine skeleton are created in a single step utilizing intramolecular [3+ 2]- cycloaddition of nonstabilized azomethine ylide as the key step. The application of the chemistry is demonstrated by synthesizing (±)-maritidine.