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

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...

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Bibliographic Details
Published in:Organic letters 2023-11, Vol.25 (46), p.8279-8283
Main Authors: Nicastri, Kate A, Gerstner, Nels C, Schomaker, Jennifer M
Format: Article
Language:English
Subjects:
Alkenes
Biological Products - pharmacology
Pactamycin - pharmacology
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c03286