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
Additional Information
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
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- 8For studies towards the total synthesis of the stephacidins or avrainvillamide, see: , , J. Am. Chem. Soc. 2003, 125, 12 080–12 081; , , , Tetrahedron Lett. 2004, 45, 4489–4493.
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- 19Proline 13 was synthesized by hydroboration and protection (TBSCl) of the corresponding enantiopure allylated proline: , , , , J. Am. Chem. Soc. 1983, 105, 5390–5398; , , , , , , , , J. Med. Chem. 1991, 34, 1777–1789; for further details, see Supporting Information.
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- 25CCDC-248 573 (23) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
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- 29J. Qian-Cutrone, personal communication. We are grateful to J. Qian-Cutrone for copies of NMR spectra in CDCl3/CD3OD (4:1) and DMSO.
- 30
- 31Detailed experimental procedures, copies of spectral data and full characterization are contained in the Supporting Information.

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