Synthesis of highly functionalised enantiopure bicyclo[3.2.1]- octane systems from carvone.
The commercially available monoterpene carvone has been efficiently converted into the tricyclo[3.2.1.0(2.7)]octane and bicyclo[3.2.1]octane systems characteristic of some biologically active compounds. The sequence used for this transformation involves as key features an intramolecular Diels-Alder reaction of a 5-vinyl-1,3-cyclohexadiene and a cyclopropane ring opening.
Abad
Antonio
A
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Dr. Moliner, 50, 46100-Burjasot, (Valencia), Spain. antonio.abad@uv.es
Agulló
Consuelo
C
Cuñat
Ana C
AC
de Alfonso
Ignacio
I
Navarro
Ismael
I
Vera
Noelia
N
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D000081005:Cyclohexane Monoterpenes; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry*; D009795:Octanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D009795:Octanes; C006923:carvone; C026728:octane