CaltechAUTHORS
Published April 29, 2022 | Version Supplemental Material
Journal Article Open

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

Creators

  • 1. ROR icon California Institute of Technology

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.

Attached Files

Supplemental Material - ol2c00948_si_001.pdf

Files

ol2c00948_si_001.pdf

Files (3.9 MB)

Name Size Download all
md5:cfb46d5a3beea7c9ea3631754236edf2
3.9 MB Preview Download

Additional details

Identifiers

Eprint ID
114383
Resolver ID
CaltechAUTHORS:20220419-936123000

Funding

Caltech Beckman Institute
Dow Chemical Company
National Defense Science and Engineering Graduate (NDSEG) Fellowship
NIH Predoctoral Fellowship
T32 GM07616
NSF Graduate Research Fellowship
DGE-1144469
NSF
CHE-1800536

Dates

Created
2022-04-20
Created from EPrint's datestamp field
Updated
2022-05-17
Created from EPrint's last_modified field