TY - JOUR
T1 - Synthetic Studies Toward Pactamycin Highlighting Oxidative C-H and Alkene Amination Technologies
AU - Su, Justin Y.
AU - Olson, David
AU - Ting, Stephen I.
AU - Du Bois, J.
PY - 2018/7/6
Y1 - 2018/7/6
N2 - A strategy enabled by C-H and alkene amination technologies for synthesizing the aminocyclitol natural product, pactamycin, is disclosed. This work features two disparate approaches for assembling the five-membered ring core of the target, the first of which utilizes acyl anion catalysis and a second involving β-ketoester aerobic hydroxylation. Installation of the C3-N bond, one of three contiguous nitrogen centers, is made possible through Rh-catalyzed allylic C-H amination of a sulfamate ester. Subsequent efforts are presented to introduce the C1,C2 cis-diamino moiety en route to pactamycin, including carbamate-mediated alkene aziridination. In the course of these studies, assembly of the core of C2-epi-pactamycate, which bears the carbon skeleton and all of the requisite nitrogen and oxygen functional groups found in the natural product, has been achieved.
AB - A strategy enabled by C-H and alkene amination technologies for synthesizing the aminocyclitol natural product, pactamycin, is disclosed. This work features two disparate approaches for assembling the five-membered ring core of the target, the first of which utilizes acyl anion catalysis and a second involving β-ketoester aerobic hydroxylation. Installation of the C3-N bond, one of three contiguous nitrogen centers, is made possible through Rh-catalyzed allylic C-H amination of a sulfamate ester. Subsequent efforts are presented to introduce the C1,C2 cis-diamino moiety en route to pactamycin, including carbamate-mediated alkene aziridination. In the course of these studies, assembly of the core of C2-epi-pactamycate, which bears the carbon skeleton and all of the requisite nitrogen and oxygen functional groups found in the natural product, has been achieved.
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U2 - 10.1021/acs.joc.8b00142
DO - 10.1021/acs.joc.8b00142
M3 - Article
C2 - 29708344
AN - SCOPUS:85049622788
VL - 83
SP - 7121
EP - 7134
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 13
ER -