We thank Dr. D. H. Huang and Dr. L. Pasternack for NMR spectroscopic assistance, and Dr. G. Siuzdak and Dr. R. Chadha for mass-spectrometric and X-ray crystallographic assistance, respectively. We are grateful to Biotage for a generous donation of process vials used extensively during these studies. Financial support for this work was provided by The Scripps Research Institute, Eli Lilly & Co, and the NIH (predoctoral fellowship to C.A.G.).
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Short, Enantioselective Total Synthesis of Stephacidin A†
Article first published online: 7 DEC 2004
DOI: 10.1002/anie.200461864
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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How to Cite
Baran, P. S., Guerrero, C. A., Ambhaikar, N. B. and Hafensteiner, B. D. (2005), Short, Enantioselective Total Synthesis of Stephacidin A. Angew. Chem. Int. Ed., 44: 606–609. doi: 10.1002/anie.200461864
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Publication History
- Issue published online: 11 JAN 2005
- Article first published online: 7 DEC 2004
- Manuscript Received: 2 SEP 2004
Keywords:
- alkaloids;
- cascade reactions;
- indoles;
- natural products;
- total synthesis
A concise route to the heptacyclic indole alkaloid stephacidin A (1) includes a simple method for the gram-scale synthesis of substituted tryptophans, a remarkable indole annulation, and the first enolate coupling of an amide to an ester. This synthesis secures the relative configuration of the natural product and paves a potential path to several of its congeners.