The Journal of organic chemistry

Synthesis of a leucomitosane via a diastereoselective radical cascade

F Brucelle, P Renaud

Index: Brucelle, Francois; Renaud, Philippe Journal of Organic Chemistry, 2013 , vol. 78, # 12 p. 6245 - 6252

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Citation Number: 6

Abstract

The preparation of trans-2, 3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones with excellent diastereomeric ratios. The radical cascade/lactamization sequence was efficiently applied to the synthesis of a 3-oxo-leucomitosane related to the mitomycin family of alkaloids.