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

Christiana N. Teijaro; Senzhi Zhao; Praveen Kokkonda; Rodrigo B. Andrade

doi:10.1055/s-0034-1378698

Synthesis, Table of Contents

Synthesis 2015; 47(11): 1547-1556
DOI: 10.1055/s-0034-1378698

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

Authors

Christiana N. Teijaro

Department of Chemistry, Temple University, 1901 N. 13^th St., Philadelphia, PA 19122, USA Email: randrade@temple.edu
Senzhi Zhao

Department of Chemistry, Temple University, 1901 N. 13^th St., Philadelphia, PA 19122, USA Email: randrade@temple.edu
Praveen Kokkonda

Department of Chemistry, Temple University, 1901 N. 13^th St., Philadelphia, PA 19122, USA Email: randrade@temple.edu
Rodrigo B. Andrade*

Department of Chemistry, Temple University, 1901 N. 13^th St., Philadelphia, PA 19122, USA Email: randrade@temple.edu

Abstract

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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.

Key words

total synthesis - natural products - strychnos alkaloids

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References

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