A straightforward total synthesis of a small panel of natural benzo[c]phenanthridines is described. The selective coupling of an aryl triflate with a bromobenzylamine by means of palladium/norbornene joint catalysis and a sequential transfer hydrogenation deliver these alkaloids in one pot. Dihydrophenanthridines initially formed undergo dehydrogenation smoothly while norbornene acts both as a catalyst for their assembly and as a sacrificial olefin in their dehydrogenation
RAPID AND CONVERGENT ASSEMBLY OF NATURAL BENZO[c]PHENANTHRIDINES BY PALLADIUM/NORBORNENE CATALYSIS / P., Deyris; T., Caneque Cobo; F., Gomes; V., Narbonne; Maestri, Giovanni; M., Maacria. - In: HETEROCYCLES. - ISSN 1881-0942. - 88:(2014), pp. 807-815. [10.3987/COM-13-S(S)62]
RAPID AND CONVERGENT ASSEMBLY OF NATURAL BENZO[c]PHENANTHRIDINES BY PALLADIUM/NORBORNENE CATALYSIS
MAESTRI, Giovanni;
2014-01-01
Abstract
A straightforward total synthesis of a small panel of natural benzo[c]phenanthridines is described. The selective coupling of an aryl triflate with a bromobenzylamine by means of palladium/norbornene joint catalysis and a sequential transfer hydrogenation deliver these alkaloids in one pot. Dihydrophenanthridines initially formed undergo dehydrogenation smoothly while norbornene acts both as a catalyst for their assembly and as a sacrificial olefin in their dehydrogenationI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
