Total Syntheses of Strasseriolide A and B, Antimalarial Macrolide Natural Products
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...
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| Veröffentlicht in: | Organic letters 2022-02, Vol.24 (5), p.1190-1194 |
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| creator | Salituro, Leah J. Pazienza, Jessica E. Rychnovsky, Scott D. |
| description | 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. |
| doi_str_mv | 10.1021/acs.orglett.1c04340 |
| format | Article |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2022-02, Vol.24 (5), p.1190-1194 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Biological Products - chemical synthesis Biological Products - chemistry Biological Products - pharmacology Macrolides - chemical synthesis Macrolides - chemistry Macrolides - pharmacology Molecular Conformation Parasitic Sensitivity Tests Plasmodium falciparum - drug effects |
| title | Total Syntheses of Strasseriolide A and B, Antimalarial Macrolide Natural Products |
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