Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine
Received: 04 February 2015
Accepted after revision: 09 March 2015
09 April 2015 (eFirst)
The first enantioselective total syntheses of (–)-alstolucinces A, B, and F, (–)-echitamidine, and (–)-N-demethylalstogucine are reported. This article details the development of our first- and second-generation approaches toward the ABCE tetracyclic core of the strychnos alkaloids and the application thereof to the aforementioned targets. Key steps involve our sequential one-pot biscyclization method that constructs the C and E rings of the tetracyclic core and Rawal’s application of the intramolecular Heck reaction to secure the pentacyclic framework common amongst all targets.