Abstract
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.
Original language | English (US) |
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Pages (from-to) | 1543-1547 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 52 |
Issue number | 5 |
DOIs | |
State | Published - Jan 28 2013 |
Externally published | Yes |
Keywords
- labdanes
- olefin isomerization
- ring expansion
- total synthesis
- vinyl oxiranes
ASJC Scopus subject areas
- Catalysis
- General Chemistry
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CCDC 906543: Experimental Crystal Structure Determination
MacK, D. J. (Contributor) & Njardarson, J. T. (Creator), Cambridge Crystallographic Data Centre, 2013
DOI: 10.5517/cczfbb1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cczfbb1&sid=DataCite
Dataset