| Autor: |
Tresse, Cédric, François‐Heude, Marc, Servajean, Vincent, Ravinder, Rubal, Lesieur, Clémence, Geiben, Lucie, Jeanne‐Julien, Louis, Steinmetz, Vincent, Retailleau, Pascal, Roulland, Emmanuel, Beau, Jean‐Marie, Norsikian, Stéphanie |
| Předmět: |
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| Zdroj: |
Chemistry - A European Journal; 3/17/2021, Vol. 27 Issue 16, p5230-5239, 10p |
| Abstrakt: |
We give a full account of the total synthesis of tiacumicin B (Tcn‐B), a natural glycosylated macrolide with remarkable antibiotic properties. Our strategy is based on our experience with the synthesis of the tiacumicin B aglycone and on unique 1,2‐cis‐glycosylation steps. We used sulfoxide anomeric leaving‐groups in combination with a remote 3‐O‐picoloyl group on the donors that allowed highly β‐selective rhamnosylation and noviosylation that rely on H‐bond‐mediated aglycone delivery. The rhamnosylated C1–C3 fragment was anchored to the C4–C19 aglycone fragment by a Suzuki–Miyaura cross‐coupling. Ring‐size‐selective Shiina macrolactonization provided a semiglycosylated aglycone that was engaged directly in the noviolysation step with a virtually total β‐selectivity. Finally, a novel deprotection method was devised for the removal of a 2‐naphthylmethyl ether on a phenol, and efficient removal of all the protecting groups provided synthetic tiacumicin B. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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