Bioinspired Total Synthesis of Agelastatin A

Bioinspired Total Synthesis of Agelastatin A

A one‐two punch: Two potentially biosynthetically relevant cyclizations of a keramadine analogue give agelastatin A (see scheme). A diastereoselective C‐ring formation, which proceeds through a 5‐exo‐trig cyclization or a Nazarov cyclization of a red‐colored N‐acyliminium intermediate, generates the...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 51; no. 28; pp. 6870 - 6873
Main Authors: Reyes, Jeremy Chris P., Romo, Daniel
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 09-07-2012
WILEY‐VCH Verlag
Subjects:
alkaloids
Alkaloids - chemical synthesis
biomimetic synthesis
Cyclization
Cyclopentanes - chemistry
Molecular Structure
N-acyliminium
Nazarov cyclization
Oxazolidinones - chemical synthesis
pyrrole-2-amino imidazole alkaloids
Silica Gel - chemistry
Stereoisomerism
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Summary:A one‐two punch: Two potentially biosynthetically relevant cyclizations of a keramadine analogue give agelastatin A (see scheme). A diastereoselective C‐ring formation, which proceeds through a 5‐exo‐trig cyclization or a Nazarov cyclization of a red‐colored N‐acyliminium intermediate, generates the three contiguous stereocenters of the cyclopentane core. A silica gel assisted cyclization of a nagelamide J analogue gives agelastatin A.
Bibliography:ArticleID:ANIE201200959
We thank the NIH (GM52964) and the Welch Foundation (A-1280) for generous support. We thank Luke Watson (NSF-REU student, CHE-0755207) for technical assistance, Dr. Lisa M. Perez and Larisa Mae Q. Reyes for helpful discussions regarding TD-DFT calculations, and Dr. Bhuvanesh Nattamai (TAMU) for obtaining the X-ray structure of 10. We acknowledge the Laboratory for Molecular Simulation (TAMU) and the Texas A&M Supercomputing Facility for providing computing resources.
ark:/67375/WNG-7MW0PP4P-Z
NIH - No. GM52964
istex:39D7BA9CC531BA03C5CBDC0AFD4109400CF40DAD
Welch Foundation - No. A-1280
We acknowledge the Laboratory for Molecular Simulation (TAMU) and the Texas A&M Supercomputing Facility for providing computing resources.
We thank the NIH (GM52964) and the Welch Foundation (A‐1280) for generous support. We thank Luke Watson (NSF‐REU student, CHE‐0755207) for technical assistance, Dr. Lisa M. Perez and Larisa Mae Q. Reyes for helpful discussions regarding TD‐DFT calculations, and Dr. Bhuvanesh Nattamai (TAMU) for obtaining the X‐ray structure of
10
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201200959