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Concise syntheses of GB22, GB13 and himgaline by cross-coupling and complete reduction

27 December 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Class III neuroactive metabolites from the bark of Galbu-limima belgraveana occur in variable distribution and are not easily procured by chemical synthesis. Here we decrease the synthetic burden of himgaline to nearly one-third of the prior best (7–9 vs. 19–31 steps) by cross-coupling high fraction aromatic (FAr) building blocks followed by com-plete, stereoselective reduction to high-fraction sp3 (Fsp3) products. This short entry into GB alkaloid space allows its extensive exploration and biological interrogation.

Keywords

Galbulimima
alkaloid
total synthesis
attached-rings
chemical space
natural products

Supplementary materials

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Description
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Title
Supporting Information for Concise syntheses of GB22, GB13 and himgaline by cross-coupling and complete reduction
Description
Experimental procedures, copies of NMR spectra, X-ray structure reports, full outlines of prior syntheses, and Matplotlib Python code.
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Version History

Dec 27, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-8nlfl
D O I: 10.26434/chemrxiv-2021-8nlfl [opens in a new tab]

Funding

National Institutes of Health
GM122606
National Science Foundation
CHE1856747
Skaggs Graduate School
Bristol Myers Squibb
Jiangsu Industrial Technology Research Institute
Shionogi & Co., Ltd.
Japan Society for the Promotion of Science
17J08551

Author’s competing interest statement

A provisional patent has been filed

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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