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

Kate A Nicastri; Nels C Gerstner; Jennifer M Schomaker

doi:10.1021/acs.orglett.3c03286

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

Journal article

Peer reviewed

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

Kate A Nicastri, Nels C Gerstner and Jennifer M Schomaker

Organic letters, Vol.25(46), pp.8279-8283

11/24/2023

DOI: 10.1021/acs.orglett.3c03286

PMCID: PMC10789149

PMID: 37997640

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https://pmc.ncbi.nlm.nih.gov/articles/PMC10789149/pdf/nihms-1955471.pdfView

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Abstract

Jogyamycin is a densely functionalized aminocyclopentitol that displays potent antiprotozoal activity. Herein, we report a route toward 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.

Alkenes

Biological Products - pharmacology

Pactamycin - pharmacology

Stereoisomerism

Details

Title: Subtitle: Progress toward the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement
Creators: Kate A Nicastri - University of Wisconsin–Madison
Nels C Gerstner - University of Wisconsin–Madison
Jennifer M Schomaker - University of Wisconsin–Madison
Resource Type: Journal article
Publication Details: Organic letters, Vol.25(46), pp.8279-8283
DOI: 10.1021/acs.orglett.3c03286
PMID: 37997640
PMCID: PMC10789149
NLM abbreviation: Org Lett
ISSN: 1523-7060
eISSN: 1523-7052
Grant note: S10 OD020022 / NIH HHS S10 RR008389 / NCRR NIH HHS F31 GM122300 / NIGMS NIH HHS R01 GM111412 / NIGMS NIH HHS
Language: English
Date published: 11/24/2023
Academic Unit: Chemistry
Record Identifier: 9984934815702771

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