Journal of Organic Chemistry 2013-06-21

Synthesis of a leucomitosane via a diastereoselective radical cascade.

François Brucelle, Philippe Renaud

Index: J. Org. Chem. 78(12) , 6245-52, (2013)

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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.