The evolution of drug-resistant strains of P. falciparum, the parasitic species responsible for the deadliest form of human malaria, has led to a demand for novel therapeutics to combat the disease. Strasseriolide B, a recently isolated macrolide from the root tissue of an unknown plant in New Zealand, demonstrates potent inhibitory activity against drug-sensitive and drug-resistant strains of the parasite. Its structure incorporates two trisubstituted E-alkenes and an anti-1,3-dimethyl array, presenting an interesting synthetic challenge. Our group has developed a convergent approach to the natural product, resulting in the first total synthesis of strasseriolide B in 17 steps LLS. Notable steps include an asymmetric conjugate addition and an intramolecular Nozaki-Hiyama-Kishi macrocyclization.

Total synthesis of strasseriolide B, a potent antimalarial macrolide

ACS Spring 2022

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