Total Synthesis of Tiacumicin B: Study of the Challenging β-Selective Glycosylations*.
antibiotics
cis-glycosylation
glycochemistry
natural products
total synthesis
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
17 Mar 2021
17 Mar 2021
Historique:
received:
27
11
2020
pubmed:
13
1
2021
medline:
13
1
2021
entrez:
12
1
2021
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 33433914
doi: 10.1002/chem.202005102
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
5230-5239Subventions
Organisme : ANR
ID : ANR-14-CE16-0019-02
Informations de copyright
© 2021 Wiley-VCH GmbH.
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