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. 2024 Jul 5;26(26):5463-5466.
doi: 10.1021/acs.orglett.4c01726. Epub 2024 Jun 21.

Enantioselective Total Syntheses of (+)-Kasugamycin and (+)-Kasuganobiosamine Highlighting a Sulfamate-Tethered Aza-Wacker Cyclization Strategy

Gour Hari Mandal  1 , Steven P Kelley  2 , Shyam Sathyamoorthi  1
Affiliations

Enantioselective Total Syntheses of (+)-Kasugamycin and (+)-Kasuganobiosamine Highlighting a Sulfamate-Tethered Aza-Wacker Cyclization Strategy

Gour Hari Mandal et al. Org Lett. .

Abstract

Here, we present the first enantioselective total syntheses of the natural products (+)-kasugamycin, a potent antifungal antibiotic, and (+)-kasuganobiosamine, a compound that results from the degradation of kasugamycin. Salient features of these syntheses include a second-generation enantioselective preparation of a kasugamine derivative (efficiency much improved relative to that of our first chiral-pool effort) and our laboratory's sulfamate-tethered aza-Wacker cyclization.

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Figures

Figure 1.
Figure 1.
Kasugamycin is an aminoglycoside natural product with potent antifungal activity and modest antibacterial activity. In soil, kasuganobiosamine is one of kasugamycin’s major degradation products.
Scheme 1.
Scheme 1.
Retrosynthetic analysis.
Scheme 2.
Scheme 2.
Opening Sequence of Reactions.
Scheme 3.
Scheme 3.
Completion of the A ring (kasugamine).
Scheme 4.
Scheme 4.
B ring derivative synthesis.
Scheme 5.
Scheme 5.
(+)-Kasugamycin end game.
Scheme 6.
Scheme 6.
Preparation of (+)-kasuganobiosamine.
See this image and copyright information in PMC

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