title: A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.
abstract: 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 Δ(4,6)-guaiadiene-9,10 diol derivatives. Regiospecific functionalization of the diene moiety installs the oxygen bridge required for the englerin tricyclic core.
authors.affiliation: Department of Chemistry, Stony Brook University, Stony Brook, New York 11733, USA.
authors.forename: Jungyong
authors.initials: J
authors.lastname: Lee
authors.forename: Kathlyn A
authors.initials: KA
authors.lastname: Parker
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D029803:Phyllanthus / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D045789:Sesquiterpenes, Guaiane; C534971:englerin A