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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Synthesis of the C1- C11 polyene fragment of apoptolidin with a new sulfur dioxide-based organic chemistry.

A new sulfur dioxide-based organic chemistry has been developed as a novel approach for the stereoselective synthesis of polyene fragments based on our one-pot, four-component synthesis of polyfunctional epsilon-alkanesulfonyl-gamma,delta-unsaturated ketones. The flexibility and efficiency of this methodology are illustrated by the preparation of (+)-methyl (2E,4E,6E,8R,9S)-9-{[(tert-butyl)dimethylsilyl]oxy}-2,4,6,8-tetramethyl-11-(triethylsilyl)undeca-2,4,6-trien-10-ynoate, a synthetic intermediate of Nicolaou and co-workers, that corresponds to the C(1)-C(11) fragment of apoptolidin, which was used by the authors in their total synthesis of this promising anticancer agent.[1]

References

  1. Synthesis of the C1-C11 polyene fragment of apoptolidin with a new sulfur dioxide-based organic chemistry. Bouchez, L.C., Vogel, P. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
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