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Total Synthesis and Structure−Activity Investigation of the Marine Natural Product Neopeltolide

2009; American Chemical Society; Volume: 131; Issue: 34 Linguagem: Inglês

10.1021/ja904604x

1943-2984

Daniel Custar, T. P. Zabawa, John Hines, Craig M. Crews, Karl A. Scheidt,

Microbial Natural Products and Biosynthesis

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.