Total Synthesis of (±)-Decinine via an Oxidative Biaryl Coupling with Defined Axial Chirality

Abstract

The total synthesis of (±)-decinine has been achieved. The key steps in the synthesis involved the formation of lasubine II via a gold catalyzed annulation of 1-(but-3-yn-1-yl)piperidine and the formation of the 12-membered ring of decinine (1) with complementary atropselectivity via a VOF3-mediated oxidative biaryl coupling reaction.

Broad Spectrum Enolate Equivalent for Catalytic Chemo-, Diastereo-, and Enantioselective Addition to N-Boc Imines

“…23 Alkaloid 6 is also an essential fragment in many bioactive compounds from the Lythraceae alkaloid family, 24 one noticeable example being (−)-decinine 7 , which can be readily synthesized from 6 . 25 The total synthesis of 6 further demonstrated the exceptional synthetic utility of our methodology incorporating ynones, in which cyclic tertiary alkaloids can be readily constructed from the common backbone 3 .…”

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

“…An intramolecular oxidation of 490 through its N -oxide forms 4-piperidone 491 , an intermediate in the total synthesis of the alkaloid (±)-decinine 492 (Scheme 162 ). 440 …”

Scholl reaction as a powerful tool for the synthesis of nanographenes: a systematic review

“…VOF 3 played a key role in realizing the total synthesis of racemic decinine. 117 In 2010, Wang and co-workers revealed a novel methodology for the oxidative coupling of polycyclic aromatic hydrocarbons via manganese dioxide-induced Scholl reaction. The phenanthrene 200 was synthesized using the MnO 2 /acid system for the coupling of stilbenes 199 (Scheme 86).…”