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Scalable De Novo Synthesis of Aldgarose and Total Synthesis of Aldgamycin N

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Späth,  Georg
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

anie202016477-s1-aldgamycin-n_si_v3.pdf
(Supplementary material), 6MB

Citation

Späth, G., & Fürstner, A. (2021). Scalable De Novo Synthesis of Aldgarose and Total Synthesis of Aldgamycin N. Angewandte Chemie International Edition, 60(14), 7900-7905. doi:10.1002/anie.202016477.


Cite as: http://hdl.handle.net/21.11116/0000-0008-4BA1-E
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.