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 |
Keywords
- labdanes
- olefin isomerization
- ring expansion
- total synthesis
- vinyl oxiranes
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)