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Tiffeneau-Demjanov rearrangement of 3'-(R)-N,N'-dibenzyloxycarbonyl-3'-aminomethyl-dihydrospectinom ycin results in ring expansion affording the homologous analog with a seven-membered sugar ring. In stark contrast, attempted rearrangement of the 3'-S-isomer leads only to epoxide formation. Deprotection of the ring-expanded homolog gives homospectinomycin. The synthesis and biological activity of this interesting new member of the spectinomycin series and the derived dihydrohomospectinomycin is detailed in this paper.

Spectinomycin modification. V. The synthesis and biological activity of spectinomycin analogs with ring-expanded sugars.