Intramolecular Diels-Alder cyclization of biodihydroxylated benzoic acid derivatives towards novel heterocyclic scaffolds

被引：20

作者：

Fischer, Thomas C. M. ^{[1
]}

Leisch, Hannes G. ^{[1
]}

Mihovilovic, Marko D. ^{[1
]}

机构：

[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria

来源：

MONATSHEFTE FUR CHEMIE | 2010年 / 141卷 / 06期

关键词：

Bioorganic chemistry; Cycloadditions; Enzymes; Biosynthesis; Dioxygenases; CHEMOENZYMATIC TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; DIHYDROXYLATION; REARRANGEMENT; ROUTE;

D O I：

10.1007/s00706-010-0291-7

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The potential of biodihydroxylated benzoic acid derivatives as versatile precursors for the construction of polycyclic scaffolds was investigated. Ralstonia eutropha B9 was used to biodihydroxylate sodium benzoate to sodium (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate in high optical purity (>95% ee). The required cyclization precursors could be obtained in moderate to excellent yields after protection of the intermediate and subsequent functional group transformation. Intramolecular Diels-Alder cylizations were carried out under thermal or microwave conditions leading to enantiomerically pure products with five chiral centers.

引用

页码：699 / 707

页数：9

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