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.
Total synthesis of the natural product benzo[j]-fluoranthene-4, 9-diol : an approach to the synthesis of oxygenated benzo[j]fluoranthenes / S. Lahore, U. Narkhede, L. Merlini, S. Dallavalle. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 78:21(2013), pp. 10860-10866. [10.1021/jo401887t]
Total synthesis of the natural product benzo[j]-fluoranthene-4, 9-diol : an approach to the synthesis of oxygenated benzo[j]fluoranthenes
S. Lahore;L. MerliniPenultimo
;S. Dallavalle
2013
Abstract
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.File | Dimensione | Formato | |
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