199280-14-3Relevant academic research and scientific papers
Total synthesis of seco (+)- and ent-(-)-oxaduocarmycin SA: Construction of the (chloromethyl)indoline alkylating subunit by a novel intramolecular aryl radical cyclization onto a vinyl chloride
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.
, p. 8868 - 8874 (2007/10/03)
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 feature 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 and 14b which were elaborated to seco-(+) and ent-(- )-oxduocarmycins, 3a and 3b. respectively. The natural enantiomer 3a was active at pM concentrations and exhibited 7-50-fold higher potentcy than its enantiomer 3b in in vitro cytotoxicity assays.
