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Synfacts 2009(10): 1059-1059
DOI: 10.1055/s-0029-1217866
DOI: 10.1055/s-0029-1217866
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Norhalichondrin B
Contributor(s):Philip Kocienski, Stewart EcclesK. L. Jackson, J. A. Henderson, H. Motoyoshi, A. J. Phillips*
University of Colorado, Boulder, USA
A Total Synthesis of Norhalichondrin B
Angew. Chem. Int. Ed. 2009, 48: 2346-2350
University of Colorado, Boulder, USA
A Total Synthesis of Norhalichondrin B
Angew. Chem. Int. Ed. 2009, 48: 2346-2350
Further Information
Publication History
Publication Date:
22 September 2009 (online)
Key words
norhalichondrin B - Achmatowicz oxidation - Nozaki-Hiyama-Kishi reaction - asymmetric crotylation - ionic hydrogenation - chromium
Significance
Norhalichondrin B is a marine polyether with potent cytotoxicity. Key to this synthetic approach are the Nozaki-Hiyama-Kishi reactions and the tandem Achmatowicz oxidation-ionic hydrogenation which form the pyranopyran systems.
Comment
The Nozaki-Hiyama-Kishi reactions were run in the presence of chiral ligand I where R was either methyl or naphthyl. The Achmatowicz oxidation-hydrogenation was highly diastereoselective (dr > 20:1).