Synthetic and Theoretical Investigations of Myrmicarin Biosynthesis

Synthetic and Theoretical Investigations of Myrmicarin Biosynthesis

Off to a good start: Use of a carefully designed building block coupled with several highly selective reactions has enabled the syntheses of the monomeric myrmicarins (see scheme) and the investigation of higher‐order oligomer synthesis by enabling access to previously unobtainable stereochemical ar...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) Vol. 49; no. 50; pp. 9693 - 9698
Main Authors: Snyder, Scott A, ElSohly, Adel M, Kontes, Ferenc
Format: Journal Article
Language:English
Published: Weinheim Wiley-VCH Verlag 10-12-2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Animals
Ants - chemistry
Biomimetics - methods
dienamines
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
iminium ion
Knorr pyrrole synthesis
myrmicarins
total synthesis
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Summary:Off to a good start: Use of a carefully designed building block coupled with several highly selective reactions has enabled the syntheses of the monomeric myrmicarins (see scheme) and the investigation of higher‐order oligomer synthesis by enabling access to previously unobtainable stereochemical arrangements. These studies, in combination with quantum chemical calculations, question whether the higher‐order structures can be obtained through acid‐promoted biomimetic synthesis.
Bibliography:http://dx.doi.org/10.1002/anie.201005825
Columbia University
Eli Lilly
Research Corporation for Science Advancement
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ArticleID:ANIE201005825
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We thank the Friesner Group (Columbia University) for generous CPU time and Michelle Lynn Hall for assistance in using the computational resources. Financial support was provided by Columbia University, Eli Lilly (New Faculty and Grantee Awards to S.A.S.), the Research Corporation for Science Advancement (Cottrell Scholar Award to S.A.S.), the National Science Foundation (Predoctoral Fellowship to A.M.E.), the Paul and Daisy Soros Foundation (Predoctoral Fellowship to A.M.E.), and Bristol-Myers Squibb (Predoctoral Fellowship to F.K.). S.A.S. is a Fellow of the Alfred P. Sloan Foundation.
These authors contributed equally to this work.
We thank the Friesner Group (Columbia University) for generous CPU time and Michelle Lynn Hall for assistance in using the computational resources. Financial support was provided by Columbia University, Eli Lilly (New Faculty and Grantee Awards to S.A.S.), the Research Corporation for Science Advancement (Cottrell Scholar Award to S.A.S.), the National Science Foundation (Predoctoral Fellowship to A.M.E.), the Paul and Daisy Soros Foundation (Predoctoral Fellowship to A.M.E.), and Bristol‐Myers Squibb (Predoctoral Fellowship to F.K.). S.A.S. is a Fellow of the Alfred P. Sloan Foundation.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201005825