Protecting-Group-Free Synthesis of Cassane-Type Furan Diterpenes via a Decarboxylative Dienone−Phenol Rearrangement
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Zentar, Houda; Arias, Fabio; Haidour, Ali; Alvarez-Manzaneda Roldán, Ramón Jesús; Chahboun, Rachid; [et al.]Date
2018-10-29Abstract
An expeditious route to obtaining cassane-type furan diterpenes starting from (+)-sclareolide, an inexpensive commercially available natural lactone, has been achieved by using a solvent-free Diels−Alder cycloaddition and an unprecedented decarboxylative dienone−phenol rearrangement as key steps. Its applicability is showcased by the first synthesis of (5α)-vouacapane-8(14),9(11)-diene. The synthesis, which requires no protecting group, is efficient and atom- and stepeconomical (10 steps, 20% global).