Total Synthesis and Structure−Activity Investigation of the Marine Natural Product Neopeltolide
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- 作者：Daniel W. Custar ; Thomas P. Zabawa ; John Hines ; Craig M. Crews ; Karl A. Scheidt
- 刊名：Journal of the American Chemical Society
- 出版年：2009
- 出版时间：September 2, 2009
- 年：2009
- 卷：131
- 期：34
- 页码：12406-12414
- 全文大小：560K
- 年卷期：v.131,no.34(September 2, 2009)
- ISSN：1520-5126
文摘
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.