Total Syntheses of Strasseriolide A and B, Antimalarial Macrolide Natural Products
Leah Salituro, Jessica E. Pazienza, Scott D. Rychnovsky
Abstract
We report the first total syntheses of strasseriolide A and B. Strasseriolide B shows potent activity against the wild-type malaria parasite Plasmodium falciparum and good activity against a chloroquine-resistant strain. A convergent strategy was envisioned with an aldehyde-acid fragment and a vinyl iodide-alcohol fragment. Both fragments were prepared using chiral pool starting materials. They were combined with a Yamaguchi esterification and cyclized with a Nozaki-Hiyama-Kishi reaction. Strasseriolide B was assembled in a 16-step LLS.
Topics & Concepts
ChemistryPlasmodium falciparumAldehydeStereochemistryTotal synthesisIodideAlcoholMalariaStrain (injury)Antimalarial AgentCombinatorial chemistryOrganic chemistryCatalysisBiologyAnatomyImmunologySynthetic Organic Chemistry MethodsMarine Sponges and Natural ProductsMicrobial Natural Products and Biosynthesis