4.4 Article

Progress towards the syntheses of Bactobolin A and C4-epi-Bactobolin A using a sulfamate-tethered aza-Wacker cyclization strategy

Journal

TETRAHEDRON
Volume 128, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.133112

Keywords

Aza-Wacker cyclization; Total synthesis; Antibiotics

Funding

  1. National Institutes of Health [R35GM142499]
  2. Tulane University

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This progress report presents the research towards Bactobolin A and C4-epi-Bactobolin A. Key intermediates were synthesized through specific chemical reactions, which can be further elaborated into the desired compounds.
We present a progress report towards Bactobolin A and C4-epi-Bactobolin A. Sulfamate-tethered azaWacker cyclization followed by a Tsuji-Wacker ketone synthesis furnishes a key tricyclic intermediate which we hypothesize can be elaborated into C4- epi-Bactobolin A. Epimerization of one of the stereocenters of this compound furnishes an intermediate which we hypothesize can be elaborated into Bactobolin A. (c) 2022 Elsevier Ltd. All rights reserved.

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