Molecular complexity from aromatics: synthesis and photoreaction of endo-tricyclo[5.2.2.0(2,6)]undecane--a stereoselective route to tricyclic framework of protoilludanes.
A stereoselective route towards protoilludanoids from simple aromatic precursor is described. The methodology involves in situ generation of spiroepoxycyclohexadienone and cycloaddition with cyclopentadiene and photochemical 1,3-acyl shift.
Singh
Vishwakarma
V
Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India. vks@chem.iitb.ac.in
Lahiri
Sanjoy
S
Pal
Shantanu
S
D001555:Benzene Derivatives / Q000737:chemistry; D005658:Fungi / Q000737:chemistry*; D007202:Indicators and Reagents; D010777:Photochemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013057:Spectrum Analysis; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D001555:Benzene Derivatives; D007202:Indicators and Reagents; D011083:Polycyclic Compounds; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C506221:protoilludane