A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules

The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs subs...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-02, Vol.140 (5), p.1956-1965
Main Authors: Robinson, Emily E, Thomson, Regan J
Format: Article
Language:English
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Summary:The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b13234