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Progress Towards the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement

09 October 2023, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Jogyamycin is a densely functionalized aminocyclopentitol that displays potent antiprotozoal activity. Herein, we report a route to this natural product that utilizes an unprecedented transformation involving a tandem Ichikawa/Winstein rearrangement to install the C-1/C-2 diamine core. Attempts to further functionalize the C-3/C-4 alkene en route to jogyamycin are also discussed.

Keywords

jogyamycin
natural product
total synthesis
aminocyclitol
Winstein
Ichikawa rearrangement

Supplementary materials

Title
Description
Actions
Title
Jogyamycin SI
Description
Supplementary information for Progress Towards the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement
Actions

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Version History

Oct 09, 2023 Version 1

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License

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

DOI

10.26434/chemrxiv-2023-gm7fh
D O I: 10.26434/chemrxiv-2023-gm7fh [opens in a new tab]

Funding

National Institute of Health
1R01GM111412
National Institute of Health
F31GM122300-02

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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