TY - JOUR
T1 - One-Pot Total Synthesis of Cannabinol via Iodine-Mediated Deconstructive Annulation
AU - Caprioglio, Diego
AU - Mattoteia, Daiana
AU - Minassi, Alberto
AU - Pollastro, Federica
AU - Lopatriello, Annalisa
AU - Muňoz, Eduardo
AU - Taglialatela-Scafati, Orazio
AU - Appendino, Giovanni
N1 - Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/8/2
Y1 - 2019/8/2
N2 - The thermal degradation of cannabichromene (CBC, 3) is dominated by cationic reactions and not by the pericyclic rearrangements observed in model compounds. The rationalization of these differences inspired the development of a process that coupled, in an aromatization-driven single operational step, the condensation of citral and alkylresorciniols to homoprenylchromenes and their in situ deconstructive annulation to benzo[c]chromenes. This process was applied to a total synthesis of cannabinol (CBN, 5) and to its molecular editing.
AB - The thermal degradation of cannabichromene (CBC, 3) is dominated by cationic reactions and not by the pericyclic rearrangements observed in model compounds. The rationalization of these differences inspired the development of a process that coupled, in an aromatization-driven single operational step, the condensation of citral and alkylresorciniols to homoprenylchromenes and their in situ deconstructive annulation to benzo[c]chromenes. This process was applied to a total synthesis of cannabinol (CBN, 5) and to its molecular editing.
UR - https://www.scopus.com/pages/publications/85070566439
U2 - 10.1021/acs.orglett.9b02258
DO - 10.1021/acs.orglett.9b02258
M3 - Article
SN - 1523-7060
VL - 21
SP - 6122
EP - 6125
JO - Organic Letters
JF - Organic Letters
IS - 15
ER -