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.
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Communication
Bioinspired Total Synthesis of Agelastatin A†
Article first published online: 11 JUN 2012
DOI: 10.1002/anie.201200959
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Reyes, J. C. P. and Romo, D. (2012), Bioinspired Total Synthesis of Agelastatin A . Angew. Chem. Int. Ed., 51: 6870–6873. doi: 10.1002/anie.201200959
- †
Publication History
- Issue published online: 4 JUL 2012
- Article first published online: 11 JUN 2012
- Manuscript Revised: 1 MAY 2012
- Manuscript Received: 3 FEB 2012
Funded by
- NIH. Grant Number: GM52964
- Welch Foundation. Grant Number: A-1280
Keywords:
- alkaloids;
- biomimetic synthesis;
- N-acyliminium;
- Nazarov cyclization;
- pyrrole-2-amino imidazole alkaloids
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.