Total synthesis of the natural product benzo[j]fluoranthene-4,9-diol: an approach to the synthesis of oxygenated benzo[j]fluoranthenes.
A synthetic sequence to the benzo[j]fluoranthene nucleus is described. Crucial steps of the procedure include a Suzuki coupling between appropriately substituted 2-bromo-acenaphthylene-1-carbaldehydes and 2-formylbenzeneboronates followed by McMurry ring closure. The synthesis represents a new approach to the benzo[j]fluoranthene ring system and specifically provides a method for the rapid preparation of differently substituted derivatives. Following this strategy, the first total synthesis of the recently isolated natural product benzo[j]fluoranthene-4,9-diol was carried out.
Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, Università di Milano , Via Celoria 2, 20133 Milano, Italy.
Santosh
S
Lahore
Umesh
U
Narkhede
Lucio
L
Merlini
Sabrina
S
Dallavalle
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002273:Carcinogens / Q000138:chemical synthesis* / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D001688:Biological Products; D002273:Carcinogens; D005449:Fluorenes; C000588744:benzo(j)fluoranthene-4,9-diol; C007738:fluoranthene