Volume 31, Issue 23
Natural Products
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ChemInform Abstract: Stereocontrolled Synthesis of a Novel Pharmacophore of the Tubulin-Depolymerizing Marine Natural Product Spongistatin.

He Huang

He Huang

Drug Discovery Program, Dep. Chem., Parker Hughes Inst., St. Paul, MN 55113, USA

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Chen Mao

Chen Mao

Drug Discovery Program, Dep. Chem., Parker Hughes Inst., St. Paul, MN 55113, USA

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Shyi-Tai Jan

Shyi-Tai Jan

Drug Discovery Program, Dep. Chem., Parker Hughes Inst., St. Paul, MN 55113, USA

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Fatih M. Uckun

Fatih M. Uckun

Drug Discovery Program, Dep. Chem., Parker Hughes Inst., St. Paul, MN 55113, USA

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First published: 08 June 2010

Abstract

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ChemInform Abstract

The stereoselective synthesis of (VI) is achieved in 11 steps starting from commercially available benzyl (R)-glycidyl ether. Key step of the synthesis is the high yielding acid-catalyzed intramolecular acetal formation to give (V). Compound (VI) causes tubulin-depolymerization and exhibits potent cytotoxicity against taxol-resistant and vincristine-resistant human cancer cells.

chemical structure image

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