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

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.

SUBMITTER: Nicastri KA

PROVIDER: S-EPMC10789149 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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

Nicastri Kate A KA Gerstner Nels C NC Schomaker Jennifer M JM

Organic letters 20231109 46

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. ...[more]

PMID: 37997640

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