Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ;
Name
367601332-MIT.pdf
Description
Full printable version
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20.5 MB
Format
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Checksum (MD5)
dfe8faec0f7ae87711f2b2a04dd68908
Author(s)
Mak, Xiao Yin
Advisor(s)
Rick L. Danheiser.
Alternative Title
Formal synthesis of (+)-FR900482
Date Issued
2008
Publisher
Massachusetts Institute of Technology
Abstract
A tandem benzannulation-ring closing metathesis strategy for the efficient synthesis of benzo-fused nitrogen heterocycles such as dihydroquinolines, benzazepines, and benzazocines has been developed. This strategy is based on the benzannulation reaction of ynamides with cyclobutenones or [alpha]-diazo ketones to generate highly-substituted aniline derivatives, which then participate in ring-closing metathesis reactions to form nitrogen heterocycles. The synthetic utility of this strategy has been demonstrated by its successful application in a formal synthesis of the natural product (+)-FR900482. In addition, an environmentally-friendly approach to the synthesis of amides and lactams has been developed using supercritical carbon dioxide as a 'green' replacement solvent. The amide products are generated from the addition of amines to ketenes, which are formed in situ from the retro-ene reaction of alkynyl ethers.
Description
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.
Vita.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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