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Virginia Tech
Chemistry of oxa- and aza-bicyclic(4.1.0)heptenes, total synthesis of (+)-pancratistatin
Abstract
dc:description.abstractVinyloxiranes 6a-b and vinylaziridines 7a-b were prepared efficiently from halocyclohexadiene-cis-diols 1. Reactions of 6 and 7 with a variety of organometallic reagents were investigated in order to determine the stereo- and regiochemistry of ring opening with carbon nucleophiles. The results indicate that 6 and 7 could serve as useful new synthons for C-disaccharides and Amaryllidaceae alkaloid syntheses. The utility of synthon 7b has been demonstrated by a concise enantiocontrolled synthesis of (+)-pancratistatin (9). The key step involved the S<sub>N</sub>2 opening of 7b with the aryl cyanocuprate derived from amide 217 to generate the pivotal cyclization precursor.
Degree
thesis:*- Name thesis:degree_name
- Ph. D.
- Level thesis:degree_level
- doctoral
- Discipline thesis:degree_discipline
- Chemistry
- Department dc:contributor.department
- Chemistry
- Grantor dc:publisher
- Virginia Tech
- Year dc:date.issued
- 1995
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Tian, Xinrong
- Chair dc:contributor.committeechair
-
- Hudlicky, Tomas
- Committee members dc:contributor.committeemember
-
- Gibson, Harry W.
- Hanson, Brian E.
- Tanko, James M.
- White, Robert H.
Rights
dc:rights- Statement dc:rights
-
- In Copyright
- Licence dc:rights.uri
- Language dc:language.iso
- en
Identifiers
dc:identifier.*- Dc Identifier Other
- etd-06062008-163626
- OAI identifier oai:identifier
- oai:vtechworks.lib.vt.edu:10919/38237