ArticleAngewandte Chemie (International ed. in English)2021
Scalable De Novo Synthesis of Aldgarose and Total Synthesis of Aldgamycin N.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed.
- Iron-Catalyzed trans-Hydrostannation of Terminal Alkynes.Angewandte Chemie (International ed. in English) · 2025Article
- Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Regioselective trans-Hydrostannation of Boron-Capped Alkynes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Scalable De Novo Synthesis of Aldgarose and Total Synthesis of Aldgamycin N.Angewandte Chemie (International ed. in English) · 2021Article
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2 authors.
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Abstract
Since the accompanying study had shown that the introduction of the eponymous aldgarose sugar to the C5-OH group of the macrocyclic aglycone of aldgamycin N is most difficult, if not even impossible, the synthesis route was revised and the glycosidation performed at an earlier stage. To mitigate the "cost" of this strategic amendment, a practical and scalable de novo synthesis of this branched octose was developed. The glycoside formation required mild conditions; it commenced with the reaction of the aglycone with the trichloroacetimidate donor to give a transient orthoester, which slowly rearranged to the desired aldgaropyranoside. The presence of the polar peripheral groups in the product did not impede the selective late-stage functionalization of the macrolide ring itself: the contained propargylic alcohol entity was readily transformed into the characteristic acyloin motif of the target by a ruthenium-catalyzed trans-hydrostannation followed by a modified Chan-Lam-type coupling.
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