Total synthesis of the taraxacine A natural product via Ag(I)-catalysed imidate-alkyne cyclization.

Autor: Zalte RR; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru., Festa AA; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru., Demidov SA; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru., Awuku SO; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru., Golubenkova AS; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru., Mironov YY; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru., Golantsov NE; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru., Storozhenko OA; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru., Novikov AP; Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky prosp., 31 Bldg. 4, 119071 Moscow, Russia., Voskressensky LG; Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia. festa-aa@rudn.ru.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2024 Dec 24. Date of Electronic Publication: 2024 Dec 24.
DOI: 10.1039/d4ob01876a
Abstrakt: A domino approach towards β-carboline natural product taraxacine A and its analogues was developed. The main step relies on a silver(I) and base co-catalysed imidate-alkyne cyclization. The reaction tolerates primary and secondary alcohols, and various substitutions in the indole are possible.
Databáze: MEDLINE