| Publication Type |
dissertation |
| School or College |
College of Science |
| Department |
Chemistry |
| Author |
Espejo, Vinson Ryan |
| Title |
The total synthesis of Kapakahines E and F: the evolution of the discovery of a unique reaction upon bromopyrroloindolines |
| Date |
2012-12 |
| Description |
The C(3)-quaternary substituted pyrroloindoline is a motif that is found in many natural products; therefore, a suitable methodology that can construct such a motif and has broad range and versatility is highly valuable. Discussed herein is the development of a novel method of the construction of C(3)-quaternary substituted pyrroloindolines and the application of the methodology to natural product synthesis. A ring contraction of C(3)-bromo pyrroloindolines to form a highly strained cyclopropane intermediate allows for the direct addition of a wide range of nucleophiles to form valuable C(3)-quaternary substituted pyrroloindolines including C(3)-N(1') heterodimeric indolines. The heterodimeric indolines synthesized using this method were then used in the total syntheses of Kapakahines E and F and toward a total synthesis of chetomin. |
| Type |
Text |
| Publisher |
University of Utah |
| Subject |
kapakahine, pyrroloindoline, total synthesis |
| Dissertation Institution |
University of Utah |
| Dissertation Name |
Doctor of Philosophy |
| Language |
eng |
| Rights Management |
Copyright © Vinson Ryan Espejo 2012 |
| Format Medium |
application/pdf |
| Format Extent |
6,556,909 bytes |
| ARK |
ark:/87278/s6r505j9 |
| Setname |
ir_etd |
| ID |
195623 |
| Reference URL |
https://collections.lib.utah.edu/ark:/87278/s6r505j9 |
