Differential Use of Anhydropyranosides for Enantiopure Routes to Bis-γ-butyrolactones: A New Approach to the Frameworks of Antibiotic and Anticancer Agents Isoavenaciolide and Ethisolide
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- 作者：Taleb H. Al-Tel ; Raed A. Al-Qawasmeh ; Salim S. Sabri ; Wolfgang Voelter
- 刊名：Journal of Organic Chemistry
- 出版年：2009
- 出版时间：July 3, 2009
- 年：2009
- 卷：74
- 期：13
- 页码：4690-4696
- 全文大小：242K
- 年卷期：v.74,no.13(July 3, 2009)
- ISSN：1520-6904
文摘
Regio- and chemoselective syntheses of enantiopure bis-furanoids are described. These compounds are chirons for several families of bioactive natural products, including isoavenaciolide and ethisolide. Reaction of a 3,4-epoxy pyran with β-ketoester dianions delivers substituted pyranosides in high yield. Cyclization then yields fused furan-pyran intermediates. Oxidation, deprotection, and rearrangement lead to bis-furanoids that bear the essential framework and stereochemistry of ethisolide and isoavenaciolide.