maoecrystal-v and tetrahydrofuran

A total synthesis of the unusual ent-kaurane maoecrystal V is described. The synthesis strategy features a counterintuitive early disconnection of the lactone subunit to a polycyclic enol ether intermediate in order to preserve the central tetrahydrofuran ring until the beginning stages of the synthesis. This strategy enables an application of C-H functionalization at the early phase of the synthesis during the construction of a dihydrobenzofuran intermediate.

Topics: Biological Products; Cyclization; Cytotoxins; Diterpenes; Furans; Lactones

An approach toward the synthesis of maoecrystal V is described. The synthetic strategy for this approach was designed to address unique challenges posed by the strained tetrahydrofuran ring at the center of the target structure.

Topics: Bridged Bicyclo Compounds; Cyclization; Diterpenes; Furans; Isodon; Molecular Structure; Stereoisomerism