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

Someshwar Nagamalla; Joel T Mague; Shyam Sathyamoorthi

doi:10.1016/j.tet.2022.133112

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

Tetrahedron. 2022 Dec 3:128:133112. doi: 10.1016/j.tet.2022.133112. Epub 2022 Oct 27.

Authors

Someshwar Nagamalla¹, Joel T Mague², Shyam Sathyamoorthi¹

Affiliations

¹ University of Kansas, Department of Medicinal Chemistry, Lawrence, KS, 66047, USA.
² Tulane University, Department of Chemistry, New Orleans, LA, 70118, USA.

Abstract

We present a progress report towards Bactobolin A and C4-epi-Bactobolin A. Sulfamate-tethered aza-Wacker 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.

Keywords: Antibiotics; Aza-Wacker cyclization; Total synthesis.

Grants and funding

R35 GM142499/GM/NIGMS NIH HHS/United States