A versatile, RCM based approach to eudesmane and dihydroagarofuran sesquiterpenoids from (−)-carvone: a formal synthesis of (−)-isocelorbicol. Issue 11 (18th March 2015)

• Record Type: Journal Article
• Authors: Senthil Kumaran, R.; Mehta, Goverdhan
• Is Part Of: Tetrahedron. Volume 71:Issue 11(2015)
• Page Start: 1718
• Page End: 1731
• Publication Date: 2015-03-18
• Subjects: Sesquiterpenoids -- Ring closure metathesis -- Oxycyclization -- Epoxidation -- Natural products synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.01.039
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An enantiospecific and diversity oriented approach to a range of functionalized eudesmane, nor-, iso -, and dihydroagarofuran frameworks from (−)-carvone is delineated. The cornerstone of this approach is the installation of the quaternary carbon center through reductive opening of the carvone epoxide and setting-up of RCM reaction to generate the bicyclic eudesmane framework. Various options like carbocation mediated oxycyclization and intramolecular hydroxy directed epoxide opening have been explored for the construction of the bridged tetrahydrofuran moiety. Among the several eudesmane and dihydroagarofurans accessed during the present study, one has been previously elaborated to isocelorbicol, thus constituting its formal synthesis. Graphical abstract: