3. A C–H activation strategy for synthesis of 8-O-methylcassiarin, a promising intermediate for total synthesis of cassiarin-type alkaloids

VARGAS VARGAS, DIDIER F.; SANTIAGO FONZO; LARGHI, ENRIQUE L; KAUFMAN, TEODORO S

Rio de Janeiro

Congreso; 35o Congresso Latinoamericano de Química; 2022

Sociedade Brasileira de Química (SQB)

The synthesis of the typical tricyclic core of cassiarin alkaloids through the use of C–H activation strategies is described. The use of an O-pivaloyl oxime (2) allowed to access the tricyclic system of 8-O-methylcassiarin (3) in 4 and 6 steps with overall yields of 19% and 26% respectively. This key intermediate could facilitate the synthesis of other natural cassiarins with additional transformations.