Synthesis 2015; 47(11): 1547-1556
DOI: 10.1055/s-0034-1378698
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© Georg Thieme Verlag Stuttgart · New York

Total Syntheses of (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine

Christiana N. Teijaro, Senzhi Zhao, Praveen Kokkonda, Rodrigo B. Andrade*
  • Department of Chemistry, Temple University, 1901 N. 13th St., Philadelphia, PA 19122, USA   Email: randrade@temple.edu
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Publication History

Received: 04 February 2015

Accepted after revision: 09 March 2015

Publication Date:
09 April 2015 (eFirst)

Abstract

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.

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