We are grateful to Dr. W. B. Schweizer for the X-ray crystallographic analysis, and to Dr. M.-O. Ebert, R. Frankenstein, P. Zumbrunnen, and R. Arnold for NMR spectroscopic studies.
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Total Synthesis of (+)-Daphmanidin E†
Article first published online: 11 OCT 2011
DOI: 10.1002/anie.201104681
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 50, Issue 48, pages 11501–11505, November 25, 2011
Additional Information
How to Cite
Weiss, M. E. and Carreira, E. M. (2011), Total Synthesis of (+)-Daphmanidin E. Angewandte Chemie International Edition, 50: 11501–11505. doi: 10.1002/anie.201104681
- †
Publication History
- Issue published online: 18 NOV 2011
- Article first published online: 11 OCT 2011
- Manuscript Received: 6 JUL 2011
Keywords:
- alkaloids;
- C
![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C coupling; - cyclization;
- natural products;
- total synthesis
Graphical Abstract
From ring to ring: The first total synthesis of (+)-daphmanidin E features rapid access to an enantiomerically pure bicyclo[2.2.2]octadione and elaboration around its periphery through the implementation of two Claisen rearrangements, the use of a copper/peptide complex for reagent-controlled stereoselective conjugate addition, a diastereoselective hydroboration, and a cobalt-catalyzed alkyl-Heck cyclization.