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

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 intram...

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Bibliographic Details
Published in:Organic letters 2017-06, Vol.19 (11), p.2985-2988
Main Authors: Potter, Tyler J, Ellman, Jonathan A
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01220