Title of article :
Unusual Dimerization of 3-Methylphenalen-1-One, Leading to a ChiralHeptacyclic Oxocin
Author/Authors :
Pogodin, S. The Hebrew University of Jerusalem - Department of Organic Chemistry, Israel , Thirumalaikumar, M. The Hebrew University of Jerusalem - Department of Organic Chemistry, Israel , Cohen, S. The Hebrew University of Jerusalem - Department of Organic Chemistry, Israel , Agranat, I. The Hebrew University of Jerusalem - Department of Organic Chemistry, Israel
Abstract :
A diastereoselective reaction of 3-methyl-1H-phenalen-1-one (6) with Lawesson’s reagent afforded 8a,15 a-dihydro-7,8a,16-trimethyl-7,16-epoxy-7H,15H,16H-naphtho[1,8-ef]phenaleno[1,2-b]oxocin-15-one (10),in 82% yield. The formation mechanism of 10 involves a Michael addition of a naphthopyrane intermediate to 6,followed by an intramolecular aldol condensation. The structure of a single enantiomer of 10 (7R, 8aR, 15aR, 16S or7S, 8aS, 15aS, 16R) was elucidated by X-ray crystallography.
Keywords :
Phenalenes , novel aromatic chemistry , diastereoselective reaction , chirality , Lawesson’s reagent , X , raycrystallography
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
