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Org Lett. 2017 Jun 2;19(11):2985-2988. doi: 10.1021/acs.orglett.7b01220. Epub 2017 May 24.

Total Synthesis of (+)-Pancratistatin by the Rh(III)-Catalyzed Addition of a Densely Functionalized Benzamide to a Sugar-Derived Nitroalkene.

Author information

1
Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8170, United States.

Abstract

Herein, we report the concise total synthesis of (+)-pancratistatin, accessed in a 10-step linear sequence from commercially available inputs. The convergent synthesis features a highly diastereoselective Rh(III)-catalyzed C-H bond addition to a d-glucose-derived nitroalkene and a late-stage intramolecular transamidation to furnish the B ring lactam.

PMID:
28537406
PMCID:
PMC5541686
DOI:
10.1021/acs.orglett.7b01220
[Indexed for MEDLINE]
Free PMC Article

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