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Synthetic Studies on Pactamycin: A Synthesis of Johnson's Intermediate
Yusuke Miura1, Hitoshi Ouchi1, Makoto Inai1
1School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Organic Letters
|April 23, 2020
Abstract:
A formal total synthesis of pactamycin (1) has been accomplished by face-selective and regioselective nitroso Diels-Alder (NDA) reaction of acyl nitroso compound 14, which contains a camphorsultam chiral auxiliary, and chiral cyclopentadiene 12. Construction of the chiral secondary alcohol of 12 was performed by (S,S)-Ts-DENEB catalyst-mediated reduction, and the NDA adduct 15a was readily converted to Johnson's intermediate 21.

