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

Rajesh R. Zalte; Alexey A. Festa; Sergei A. Demidov; Samuel O. Awuku; Alexandra S. Golubenkova; Yuri Yu. Mironov; Nikita E. Golantsov; Olga A. Storozhenko; Anton P. Novikov; Leonid G. Voskressensky

doi:10.1039/D4OB01876A

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

Rajesh R. Zalte,^a Alexey A. Festa,

*^a Sergei A. Demidov,^a Samuel O. Awuku,

^a Alexandra S. Golubenkova,^a Yuri Yu. Mironov,^a Nikita E. Golantsov,^a Olga A. Storozhenko,^a Anton P. Novikov

^b and Leonid G. Voskressensky^a

Author affiliations

* Corresponding authors

^a Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia
E-mail: festa-aa@rudn.ru

^b Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky prosp., 31 Bldg. 4, 119071 Moscow, Russia

Abstract

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.

Organic & Biomolecular Chemistry

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

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

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