We gratefully acknowledge the NIH (GM090153) for funding. M.D.B. is an Early Career Scientist of the Howard Hughes Medical Institute. We also acknowledge Kaitlyn Gray for preliminary studies of the transformation of MIDA boronates into vinyliodides.
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Communication
Total Synthesis of Synechoxanthin through Iterative Cross-Coupling†
Article first published online: 16 JUN 2011
DOI: 10.1002/anie.201102688
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Fujii, S., Chang, S. Y. and Burke, M. D. (2011), Total Synthesis of Synechoxanthin through Iterative Cross-Coupling. Angew. Chem. Int. Ed., 50: 7862–7864. doi: 10.1002/anie.201102688
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Publication History
- Issue published online: 12 AUG 2011
- Article first published online: 16 JUN 2011
- Manuscript Received: 19 APR 2011
Funded by
- NIH. Grant Number: GM090153
- Howard Hughes Medical Institute
Keywords:
- antioxidants;
- boronates;
- iterative cross-coupling;
- synechoxanthin;
- total synthesis
The choice is yours: The first total synthesis of the antioxidant carotenoid synechoxanthin was achieved through a novel iterative cross-coupling approach in which the polarity of the bifunctional building blocks is reversed to match the preferred polarity for C![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C bond formation (see scheme). The convergent, stereocontrolled, and flexible nature of this synthesis enables systematic studies of the biological activities of this natural product.