Synthesis of strychnine via the Wieland-Gumlich aldehyde

Metallacycle-mediated cross-coupling in natural product synthesis

“…175–185 Moving forward with the development of methods for Co-mediated [2+2+2] annulation between enynes and alkynes, Vollhardt’s group demonstrated the ability to employ an indole double bond in the annulation process and highlighted the application of this coupling chemistry in the context of a formal total synthesis of strychnine. 186, 187 As illustrated in Figure 59B, union of 149 with acetylene ( 71 ) delivered the tetracyclic product 150 in 46% yield.…”

Kein Ende für Totalsynthesen von Strychnin in Sicht? Lektionen für Strategien und Methoden in der Totalsynthese

“…[40,44] 3. Wir berücksichtigen Synthesen, die neue Wege zum Aufbau des komplexen Strychningerüstes einführen und allgemeine Erkenntnisse über chemische Synthesestrategien und/oder -methoden lehren.…”

Bitter Nemesis. The Intimate History of Strychnine. By John Buckingham.

“…Imagine comparing the 14-step total synthesis of quinine by Padwa, [9] published last year, with Woodwards 28-step synthesis nearly 50 years ago, [10][11][12] which was universally hailed with triumph and with awe. Indeed, it took 38 more years subsequent to Woodwards brilliant success until the next reported synthesis of strychnine (in 25 steps) by Magnus [13,14] in 1992. Nevertheless, Bitter Nemesis is the wonderful result of Buckinghams passions and perspectives.…”