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Synfacts 2009(10): 1059-1059  
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 Eccles
K. 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  
Further Information

Publication History

Publication Date:
22 September 2009 (online)

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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).

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