Abstract
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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 7121-7134 |
| Number of pages | 14 |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue number | 13 |
| DOIs | |
| State | Published - Jul 6 2018 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthetic Studies Toward Pactamycin Highlighting Oxidative C-H and Alkene Amination Technologies. / Su, Justin Y.; Olson, David; Ting, Stephen I.; Du Bois, J.
In: Journal of Organic Chemistry, Vol. 83, No. 13, 06.07.2018, p. 7121-7134.Research output: Contribution to journal › Article
}
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.
UR - http://www.scopus.com/inward/record.url?scp=85049622788&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85049622788&partnerID=8YFLogxK
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 -