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Paper | Special issue | Vol 99, No. 1, 2019, pp.389-403
Published online, 5th November, 2018
DOI: 10.3987/COM-18-S(F)32
Model Studies for the Total Synthesis of 11-Demethoxymyrtoidine and Myrtoidine

Amaan M. Kazerouni, Danny E. Mancheno, and Simon B. Blakey*

*Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, U.S.A.

Abstract

The malagasy alkaloids, isolated in the 1990s from Madagascan shrub Strychnos myrtoides, are a family of strychnos alkaloids whose members have been reported to potentiate chloroquine activity against resistant strains of Plasmodium falciparum malaria. 11-Demethoxymyrtoidine, myrtoidine, and malagashanine were identified as the major components of the shrub used by local populations to treat malaria. Herein we report our studies on model systems to construct the EF dihydropyran lactone moiety present in 11-demethoxymyrtoidine and myrtoidine, and initial studies toward the application of these strategies to the total synthesis of these alkaloids.