Construction of the 5, 10b??Phenanthridine Skeleton Using [3+ 2]??Cycloaddition of a Non??Stabilized Azomethine Ylide: Total Synthesis of (±)??Maritidine and (±)?? …

G Pandey, NR Gupta, SR Gadre

Index: Pandey, Ganesh; Gupta, Nishant R.; Gadre, Smita R. European Journal of Organic Chemistry, 2011 , # 4 p. 740 - 750

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Citation Number: 13

Abstract

Abstract Vicinal quaternary and tertiary stereocenters of the 5, 10b-phenanthridine skeleton 1 are constructed simultaneously in one step by the [3+ 2]-cycloaddition of non-stabilized azomethine ylide 9, generated by sequential double desilylation of 10 utilizing silver (I) fluoride as a one-electron oxidant. The regio-as well as stereochemical origin of this cycloaddition reaction is explained through a favorable transition state 9 ″. The strategy ...