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University of Illinois at Urbana-Champaign
The Asymmetric Total Synthesis of Cephalotaxine
Abstract
dc:descriptionA unique method for the formation of [3]benzazepines, via the [3,3]-sigmatropic rearrangement of 1-vinyl-2-aryl-aziridines, has been developed and applied to the synthesis of the Cephalotaxus alkaloids. The synthetic approach begins with D-ribose and utilizes the [3,3] sigmatropic rearrangement of a highly functionalized 1-vinyl-2-aryl aziridine and a diastereoselective intermolecular [3+2] cycloaddition of a non-stabilized azomethine ylide as the key steps. This work has resulted in an asymmetric total synthesis of cephalotaxine in 24 steps and 0.9% overall yield.
Degree
thesis:*- Name thesis:degree_name
- Ph.D.
- Level thesis:degree_level
- Dissertation
- Discipline thesis:degree_discipline
- Chemistry
- Grantor
- University of Illinois at Urbana-Champaign
- Year dc:date
- 2015
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Eckelbarger, Joseph David
- Contributors dc:contributor
-
- Gin, David Y.
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI3223583
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84220