New syntheses of biliverdins, corroles and azaporphyrins from 1,19-dibromo-ac-biladiene salts
Treatment of the readily available, 1,19 dibromo-ac-biladiene dihydrobromide salts 3 with dimethyl sulfoxide (DMSO) in presence of a catalytic amount of toluene-p-sulfonic acid affords symmetrical and unsymmetrical biliverdins 4 in excellent yield; unsymmetrically substituted 1,19 dibromo-ac-biladiene dihydrobromide 3c was prepared in a stepwise fashion via a tripyrrin salt. Under appropriate reaction conditions, the ac-biladiene dihydrobromides were also converted in modest yields into the corroles 5 and the azaporphyrins 6. © 1994 by the Royal Society of Chemistry. All Rights Reserved.
Publication Source (Journal or Book title)
Journal of the Chemical Society, Perkin Transactions 1
Pandey, R., Gerzevske, K., Zhoue, H., & Smith, K. (1994). New syntheses of biliverdins, corroles and azaporphyrins from 1,19-dibromo-ac-biladiene salts. Journal of the Chemical Society, Perkin Transactions 1, 971-977. https://doi.org/10.1039/P19940000971