- Library Home /
- Search Collections /
- Open Collections /
- Browse Collections /
- UBC Theses and Dissertations /
- Efforts toward the total synthesis of mitomycins
Open Collections
UBC Theses and Dissertations
UBC Theses and Dissertations
Efforts toward the total synthesis of mitomycins Vialettes, Anne
Abstract
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.
Item Metadata
Title |
Efforts toward the total synthesis of mitomycins
|
Creator | |
Publisher |
University of British Columbia
|
Date Issued |
2009
|
Description |
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.
|
Extent |
3390053 bytes
|
Genre | |
Type | |
File Format |
application/pdf
|
Language |
eng
|
Date Available |
2009-05-13
|
Provider |
Vancouver : University of British Columbia Library
|
Rights |
Attribution-NonCommercial-NoDerivatives 4.0 International
|
DOI |
10.14288/1.0061600
|
URI | |
Degree | |
Program | |
Affiliation | |
Degree Grantor |
University of British Columbia
|
Graduation Date |
2009-11
|
Campus | |
Scholarly Level |
Graduate
|
Rights URI | |
Aggregated Source Repository |
DSpace
|
Item Media
Item Citations and Data
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International