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

被引：15

作者：

Al-Tel, Taleb H. ^{[1
]}

Al-Qawasmeh, Raed A. ^{[2
]}

Sabri, Salim S. ^{[1
]}

Voelter, Wolfgang ^{[3
]}

机构：

[1] Univ Sharjah, Coll Pharm, Sharjah, U Arab Emirates

[2] Univ Jordan, Dept Chem, Amman, Jordan

[3] Univ Tubingen, Inst Physiol Chem, D-72076 Tubingen, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 13期

关键词：

1,3-OXYGEN-TO-CARBON ALKYL SHIFTS; STEREOSELECTIVE-SYNTHESIS; DIACETONE GLUCOSE; LACTONES; STRATEGY; (+)-DIHYDROCANADENSOLIDE; AVENACIOLIDE; FURANOIDS;

D O I：

10.1021/jo900192a

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

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 beta-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 stercochemistry of ethisolide and isoavenaciolide.

引用

页码：4690 / 4696

页数：7

共 32 条

[1]

Al-Qawasmeh RA, 1999, CHEM LETT, P541

[2]

STEREOSELECTIVE SYNTHESIS OF BETA-OXY-GAMMA-BUTYROLACTONES AND ALPHA-METHYLENE-GAMMA-BUTYROLACTONES ON PYRANOSE TEMPLATES [J].