3 years ago

A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules

A Strategy
for the Convergent and Stereoselective
Assembly of Polycyclic Molecules
Regan J. Thomson, Emily E. Robinson
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b13234

DOI: 10.1021/jacs.7b13234

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