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A Formal Synthesis of (−)-Englerin A by Relay Ring Closing Metathesis and Transannular Etherification
- Lee, Jungyong, Parker, Kathlyn A.
- Organic letters 2012 v.14 no.11 pp. 2682-2685
- chemical reactions, moieties, organic compounds, oxygen, regioselectivity
- A bicyclization approach to englerin A has culminated in a formal asymmetric total synthesis. Key transformations in the 10-step sequence are a regiospecific epoxide opening and a relay ene-yne-ene metathesis that converts linear substrates specifically to Δ⁴,⁶-guaiadiene-9,10 diol derivatives. Regiospecific functionalization of the diene moiety installs the oxygen bridge required for the englerin tricyclic core.