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Enantioselective synthesis of spliceostatin E and evaluation of biological activity.

ABSTRACT: An enantioselective total synthesis of spliceostatin E has been accomplished. The ?-lactone unit A was constructed from readily available (R)-glycidyl alcohol using a ring-closing olefin metathesis as the key reaction. A cross-metathesis of ring A containing ?-lactone and the functionalized tetrahydropyran B-ring provided spliceostatin E. Our biological evaluation of synthetic spliceostatin E revealed that it does not inhibit splicing in vitro and does not impact speckle morphology in cells. Spliceostatin E was reported to possess potent antitumor activity.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC4260646 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of spliceostatin E and evaluation of biological activity.

Ghosh Arun K AK Veitschegger Anne M AM Sheri Venkata Reddy VR Effenberger Kerstin A KA Prichard Beth E BE Jurica Melissa S MS

Organic letters 20141125 23

An enantioselective total synthesis of spliceostatin E has been accomplished. The δ-lactone unit A was constructed from readily available (R)-glycidyl alcohol using a ring-closing olefin metathesis as the key reaction. A cross-metathesis of ring A containing δ-lactone and the functionalized tetrahydropyran B-ring provided spliceostatin E. Our biological evaluation of synthetic spliceostatin E revealed that it does not inhibit splicing in vitro and does not impact speckle morphology in cells. Spl ...[more]

PMID: 25423085

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