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• W2951593313 startingPage "8868" @default.
• W2951593313 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 and 14b which were elaborated to seco-(+) and ent-(−)-oxaduocarmycins, 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." @default.
• W2951593313 created "2019-06-27" @default.
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• W2951593313 date "1997-12-01" @default.
• W2951593313 modified "2023-09-27" @default.
• W2951593313 title "Total Synthesis of Seco (+)- and<i>ent</i>-(−)-Oxaduocarmycin SA: Construction of the (Chloromethyl)indoline Alkylating Subunit by a Novel Intramolecular Aryl Radical Cyclization onto a Vinyl Chloride" @default.
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• W2951593313 doi "https://doi.org/10.1021/jo971880b" @default.
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