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Daniel J. Mack and Prof. Jon T. Njardarson Syntheses and Structural Confirmations of Members of a Heterocycle-Containing Family of Labdane Diterpenoids Angewandte Chemie International Edition 52

Version of Record online: 17 DEC 2012 | DOI: 10.1002/anie.201208412

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Building with berries! Several labdane natural products have been synthesized for the first time by the combination of a copper-catalyzed vinyl oxirane ring expansion reaction with an abundant, inexpensive, chiral natural source (juniper berries; see scheme). These expedient (1–5 step) syntheses have resulted in the structural confirmations of five natural products and one reassignment. Reagent-controlled oxidation and 1,3-diene isomerization results are also presented.

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