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Total synthesis and structure-activity investigation of the marine natural product neopeltolide.

ABSTRACT: The total synthesis and biological evaluation of neopeltolide and analogs are reported. The key bond-forming step utilizes a Lewis acid-catalyzed intramolecular macrocyclization that installs the tetrahydropyran ring and macrocycle simultaneously. Independent of each other, neither the macrolide nor the oxazole side chain substituents of neopeltolide can inhibit the growth of cancer cell lines. The biological data of the analogs indicate that alterations to either the ester side chain or the stereochemistry of the macrolide result in a loss of biological activity.

SUBMITTER: Custar DW

PROVIDER: S-EPMC2735232 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Total synthesis and structure-activity investigation of the marine natural product neopeltolide.

Custar Daniel W DW Zabawa Thomas P TP Hines John J Crews Craig M CM Scheidt Karl A KA

Journal of the American Chemical Society 20090901 34

The total synthesis and biological evaluation of neopeltolide and analogs are reported. The key bond-forming step utilizes a Lewis acid-catalyzed intramolecular macrocyclization that installs the tetrahydropyran ring and macrocycle simultaneously. Independent of each other, neither the macrolide nor the oxazole side chain substituents of neopeltolide can inhibit the growth of cancer cell lines. The biological data of the analogs indicate that alterations to either the ester side chain or the ste ...[more]

PMID: 19663512

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