Synthesis of Polycyclic Benzofused Nitrogen Heterocycles via a Tandem Benzannulation/Ring-Closing Metathesis Strategy. Application in a Formal Synthesis of (+)-
Name
Danheiser Benzann JOC 2011 76 1852 Revised.pdf
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1.64 MB
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Author(s)
Mak, Xiao Yin
Crombie, Aimee L.
Danheiser, Rick Lane
Date Issued
February 2011
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society
Citation
Mak, Xiao Yin, Aimee L. Crombie, and Rick L. Danheiser. “Synthesis of Polycyclic Benzofused Nitrogen Heterocycles via a Tandem Ynamide Benzannulation/Ring-Closing Metathesis Strategy. Application in a Formal Total Synthesis of (+)-FR900482.” The Journal of Organic Chemistry 76.6 (2011): 1852–1873.
Version
Author's final manuscript
Abstract
A two-stage “tandem strategy” for the synthesis of benzofused nitrogen heterocycles is described that is particularly useful for the construction of systems with a high level of substitution on the benzenoid ring. The first stage in the strategy involves a
benzannulation based on the reaction of cyclobutenones with ynamides. This cascade process proceeds via a sequence of four pericyclic reactions and furnishes a multiply substituted aniline derivative which can bear a variety of functionalized substituents at the position ortho to the nitrogen. In the second stage of the tandem strategy, ringclosing metathesis generates the nitrogen heterocyclic ring. This two-step sequence provides efficient access to highly substituted dihydroquinolines, benzazepines, benzazocines, and related benzofused nitrogen heterocyclic systems. The application of this chemistry in a concise formal total synthesis of the anticancer agents (þ)-FR900482 and (þ)-FR66979 is described.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/jo2000308
