Fig. 3: Retrosynthetic analysis of SPM-1 and SPM-2.
From: Synthesis of macrocyclic nucleoside antibacterials and their interactions with MraY
The macrocycle and the piperidine ring of A are constructed simultaneously by double-reductive amination of aminodialdehyde B. The dialdehyde B arises from a cyclopentene C by oxidative cleavage of olefin. A cyclopentenyl group is introduced by an asymmetric Tsuji–Trost allylic alkylation reaction of D and racemic cyclopentene E.
