Total Syntheses of Strasseriolide A and B, Antimalarial Macrolide Natural Products
Leah J Salituro1, Jessica E Pazienza1, Scott D Rychnovsky1
1Department of Chemistry, University of California at Irvine, 1102 Natural Sciences II, Irvine, California 92697, United States.
Organic Letters
|January 31, 2022
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.

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