Synthesis of Noraugustamine and Development of an Oxidative Heck/Aza-Wacker Cascade Cyclization

Creators: Holman, Karli R.; Stanko, Allison M.; Richter, Matthieu J. R.; Feng, Sean S.; Gessesse, Mahideremariyam N.; Reisman, Sarah E.

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Abstract

Radical and transition metal-catalyzed cascade cyclization strategies were investigated with respect to the synthesis of the tetracyclic core of the augustamine-type Amaryllidaceae alkaloids. These studies resulted in the synthesis of noraugustamine and the development of an oxidative Heck/aza-Wacker cascade forming two rings, a C–N bond, and an all-carbon quaternary center in a single step.

Additional Information

© 2022 American Chemical Society. Received: March 16, 2022; Published: April 15, 2022. The authors thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. This research also benefited from the use of instrumentation made available by the Caltech CCE Multiuser Mass Spectrometry Laboratory. The Beckman Institute and Dow are gratefully acknowledged for their support of the X-ray Crystallography Facility at Caltech. K.R.H. was supported by a National Defense Science and Engineering Graduate Fellowship and an National Institutes of Health/National Research Service Award training grant (T32 GM07616). S.S.F. was supported by a National Science Foundation (NSF) Graduate Research Fellowship (DGE-1144469). S.E.R. acknowledges financial support from the NSF (CHE-1800536). The authors declare no competing financial interest. CCDC 2150221 contains the supplementary crystallographic data for this paper.

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