Bouanou H1, Gil JA1, Alvarez-Manzaneda R2, Chahboun R1, Alvarez-Manzaneda E1.
J Org Chem. 2016 Oct 21;81(20):10002-10008. Epub 2016 Oct 7.Treatment of (-)-sclareol and related compounds with lead tetraacetate affords tetracyclic compounds bearing a 2,8-dioxabicyclo[5.2.0]nonane moiety with complete regio- and stereoselectivity. This process, which is also applicable to 1,5-diols with a similar substitution pattern, facilitates the development of efficient syntheses toward oxepane terpenoids, such as aplysistatin derivatives.