Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity | Zendy

Arun K. Ghosh | Zendy; Anne M. Veitschegger | Zendy; Venkata Reddy Sheri | Zendy; Kerstin A. Effenberger | Zendy; Beth E. Prichard | Zendy; Melissa S. Jurica | Zendy

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Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity

Author(s) -

Arun K. Ghosh,

Anne M. Veitschegger,

Venkata Reddy Sheri,

Kerstin A. Effenberger,

Beth E. Prichard,

Melissa S. Jurica

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol503127r

Subject(s) - enantioselective synthesis , chemistry , ring closing metathesis , tetrahydropyran , stereochemistry , ring (chemistry) , metathesis , lactone , combinatorial chemistry , olefin metathesis , organic chemistry , catalysis , polymer , polymerization

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. Spliceostatin E was reported to possess potent antitumor activity.

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