Total synthesis of seco (+)-and ent-(-)-oxaduocarmycin SA: construction of the (chloromethyl) indoline alkylating subunit by a novel intramolecular aryl radical …

…, DA Johnson, JH Kennedy, F Mohamadi…

Index: Patel, Vinod F.; Andis, Sherri L.; Enkema, Julia K.; Johnson, David A.; Kennedy, Joseph H.; Mohamadi, Fariborz; Schultz, Richard M.; Soose, Daniel J.; Spees, Michael M. Journal of Organic Chemistry, 1997 , vol. 62, # 25 p. 8868 - 8874

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Citation Number: 54

Abstract

A practical, total synthesis of seco-(+)-oxaduocarmycin 3a, an analogue of the highly cytotoxic natural product, duocarmycin SA (1), is described. The 13-step synthesis features a novel and efficient intramolecular aryl radical cyclization onto a vinyl chloride as a direct entry to the (chloromethyl) indoline alkylating subunit 14. Subsequent resolution, utilizing a preparative Chiralpak AD column, provided enantiomerically pure alkylating subunits 14a ...