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Synthetic Study on Pactamycin: Stereoselective Synthesis of the Cyclopentane Core Framework

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journal contribution
posted on 12.06.2017, 12:03 by Atsumi Goto, Satoshi Yoshimura, Yuta Nakao, Makoto Inai, Tomohiro Asakawa, Masahiro Egi, Yoshitaka Hamashima, Mitsuru Kondo, Toshiyuki Kan
The cyclopentane core framework 23 of pactamycin (1) was synthesized in 14 steps from symmetric cyclohexadiene 11. Our synthetic strategy features Rh-mediated catalytic desymmetrization of 10 via aziridination and then regioselective ring-opening reaction of sulfonylaziridine 9 with NaN3, ring-contraction of cyclohexene 14 by ozonolysis followed by intramolecular aldol reaction, and stereoselective construction of the sequential tetrasubstituted carbons by dihydroxylation and methylation reaction. Stereospecific incorporation of amine on tetrasubstituted carbon was achieved by Curtius rearrangement and subsequent carbamide formation.