Protecting-Group-Free Synthesis of Cassane-Type Furan Diterpenes via a Decarboxylative Dienone–Phenol Rearrangement

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. It...

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Bibliographic Details
Published in:Organic letters 2018-11, Vol.20 (22), p.7007-7010
Main Authors: Zentar, Houda, Arias, Fabio, Haidour, Ali, Alvarez-Manzaneda, Ramón, Chahboun, Rachid, Alvarez-Manzaneda, Enrique
Format: Article
Language:English
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Summary: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 step-economical (10 steps, 20% global).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02867