This research was supported by the National Cancer Institute (NCI CA110246), Eli Lilly & Co under the auspices of the Lilly Awardee Program (to A.J.P.), and in part by The American Chemical Society Petroleum Research Fund (ACS PRF 38856-G1). We thank Prof. Robert H. Grubbs and Dr. Ian C. Stewart (Caltech), Materia Inc. for catalyst 41, Prof. Yoshito Kishi (Harvard), and Professors John Blunt and Murray Munro (Canterbury) for copies of spectra.
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Communication
A Total Synthesis of Norhalichondrin B†
Article first published online: 11 FEB 2009
DOI: 10.1002/anie.200806111
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Jackson, K., Henderson, J., Motoyoshi, H. and Phillips, A. (2009), A Total Synthesis of Norhalichondrin B. Angewandte Chemie International Edition, 48: 2346–2350. doi: 10.1002/anie.200806111
- †
Publication History
- Issue published online: 10 MAR 2009
- Article first published online: 11 FEB 2009
- Manuscript Received: 15 DEC 2008
Funded by
- National Cancer Institute. Grant Number: NCI CA110246
- Eli Lilly
- The American Chemical Society Petroleum Research Fund. Grant Number: ACS PRF 38856-G1
Keywords:
- metathesis;
- polyethers;
- pyrans;
- total synthesis
Graphical Abstract
Four corners: The syntheses of four key building blocks for the total synthesis of norhalichondrin B (see structure) are described. The assembly of these subunits into the natural product is also reported. Key features of the synthesis are the use of the Achmatowicz oxidation/ionic hydrogenation for the synthesis of pyrans and pyranopyrans, and the application of tandem metathesis for the synthesis of pyranopyrans.
Abstract
Four corners: The syntheses of four key building blocks for the total synthesis of norhalichondrin B (see structure) are described. The assembly of these subunits into the natural product is also reported. Key features of the synthesis are the use of the Achmatowicz oxidation/ionic hydrogenation for the synthesis of pyrans and pyranopyrans, and the application of tandem metathesis for the synthesis of pyranopyrans.