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Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches

Author

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  • Barry M. Trost

    (Stanford University, Stanford, California 94305-5080, USA)

  • Guangbin Dong

    (Stanford University, Stanford, California 94305-5080, USA)

Abstract

Economical with the atoms The ideal in organic synthesis is to prepare complex molecules in the smallest possible number of steps. Also important is atom economy — limiting waste by ensuring that most of atoms present in the reactants end up in the product. Barry Trost and Guangbin Dong demonstrate these principles to good effect in a synthesis of the naturally occurring compound bryostatin 16 that takes about half as many steps as previous methods. A key reaction is the formation of a large ring, in a palladium-catalysed reaction between two alkynes (hydrocarbons containing carbon-carbon triple bonds). The bryostatins, a group of macrolide lactones originally isolated from coral-like marine organisms, display a range of biological activities including cytotoxicity, and have potential in anticancer and memory enhancement therapies.

Suggested Citation

  • Barry M. Trost & Guangbin Dong, 2008. "Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches," Nature, Nature, vol. 456(7221), pages 485-488, November.
    • Handle: RePEc:nat:nature:v:456:y:2008:i:7221:d:10.1038_nature07543
    DOI: 10.1038/nature07543
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