Asymmetric synthesis of (+)-17-epi-methoxy-kauran-3-one through tandem oxidative polycyclization-pinacol processElectronic supplementary information (ESI) available. See DOI: 10.1039/c6ob01142j

• Main Authors: Maertens, Gaëtan, Desjardins, Samuel, Canesi, Sylvain
• Format: Journal Article
• Published: 12.07.2016
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c6ob01142j

A synthesis of (+)-17- epi -methoxy-kauran-3-one, an O -methylated isomer of the natural diterpene 17-hydroxy-kauran-3-one, has been achieved. The strategy is based on a diastereoselective oxidative polycyclization-pinacol tandem process consisting of transforming a functionalized phenol into a compact and complex tetracycle, which represents the main core of kaurane family members. The synthesis also includes an enantioselective Yamamoto's allylation, a diastereoselective Ru-catalyzed hydrocyanation, a ring-closing metathesis and a reductive isomerization process as key steps. The structure of our synthetic substrate was determined through comparison with an O -methylated derivative of the natural compound. A synthesis of (+)-17- epi -methoxy-kauran-3-one, an O -methylated isomer of the natural diterpene 17-hydroxy-kauran-3-one, has been achieved. The strategy is based on a diastereoselective oxidative polycyclization-pinacol tandem process consisting in transforming a functionalized phenol into a compact and complex tetracycle.