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

Holman, Karli R. and Stanko, Allison M. and Richter, Matthieu J. R. and Feng, Sean S. and Gessesse, Mahideremariyam N. and Reisman, Sarah E. (2022) Synthesis of Noraugustamine and Development of an Oxidative Heck/Aza-Wacker Cascade Cyclization. Organic Letters, 24 (16). pp. 3019-3023. ISSN 1523-7060. doi:10.1021/acs.orglett.2c00948. https://resolver.caltech.edu/CaltechAUTHORS:20220419-936123000

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.2c00948DOIArticle
ORCID:
AuthorORCID
Holman, Karli R.0000-0001-6424-9479
Stanko, Allison M.0000-0003-0576-3739
Richter, Matthieu J. R.0000-0001-7957-3474
Feng, Sean S.0000-0002-8095-6402
Gessesse, Mahideremariyam N.0000-0001-9732-7488
Reisman, Sarah E.0000-0001-8244-9300
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.
Funders:
Funding AgencyGrant Number
Caltech Beckman InstituteUNSPECIFIED
Dow Chemical CompanyUNSPECIFIED
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
NIH Predoctoral FellowshipT32 GM07616
NSF Graduate Research FellowshipDGE-1144469
NSFCHE-1800536
Subject Keywords:Azides, Atmospheric chemistry, Cyclization, Selectivity, Anions
Issue or Number:16
DOI:10.1021/acs.orglett.2c00948
Record Number:CaltechAUTHORS:20220419-936123000
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20220419-936123000
Official Citation:Synthesis of Noraugustamine and Development of an Oxidative Heck/Aza-Wacker Cascade Cyclization. Karli R. Holman, Allison M. Stanko, Matthieu J. R. Richter, Sean S. Feng, Mahideremariyam N. Gessesse, and Sarah E. Reisman. Organic Letters 2022 24 (16), 3019-3023; DOI: 10.1021/acs.orglett.2c00948
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:114383
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:20 Apr 2022 14:13
Last Modified:17 May 2022 16:48

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