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Efforts toward the total synthesis of mitomycins

University of British Columbia

This thesis describes our efforts toward the total synthesis of mitomycins. The centerpiece of our route to the target molecule is a homo-Brook mediated aziridine fragmentation, developed in our laboratory. The aziridine moiety of the target molecule was installed through an intramolecular iodoamidification of an olefin. The crystalline triazoline intermediate, available before the homo-Brook rearrangement, was obtained after Reetz allylation on an aldehyde followed by a intramolecular 1,3-diploar cycloaddition of an azido unit onto a terminal olefin. The aldehyde intermediate was synthesized in 9 steps involving a Mitsunobu reaction, a Claisen rearrangement and a Lemieux-Johnson oxidation from readily commercially available products.

Thesis/Dissertation

application/pdf

2009-05-13

Attribution-NonCommercial-NoDerivatives 4.0 International

http://hdl.handle.net/2429/7908

Chemistry

University of British Columbia

UBCV

http://creativecommons.org/licenses/by-nc-nd/4.0/