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Alexander Breder, Dr. Gary M. Chinigo, Dr. Andrew W. Waltman and Prof. Dr. Erick M. Carreira Towards the Synthesis of Massadine: A Unified Strategy for the Stereoselective Synthesis of the Carbocyclic C,D-Ring Subunit Chemistry - A European Journal 17

Version of Record online: 20 SEP 2011 | DOI: 10.1002/chem.201101862

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Tying the knot: An efficient strategy for the stereocontrolled synthesis of the spirocyclic C,D-ring subunit of massadine (1) has been developed. Key operations in the construction of the D-ring were a Fleming norbornyl rearrangement, a highly regioselective endgroup-differentiating ozonolysis, and a radical decarboxylative hydroxylation. The spirocyclization (C-ring) was realized through a chemoselective oxidation of a primary alcohol.

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