Synthesis of aromatic spiroacetals related to γ-rubromycin based on a 3H-spiro[1-benzofuran-2,2′-chromane] skeleton
| Autor: | Margaret A. Brimble, Kit Yee Tsang |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
chemistry.chemical_classification
Stereochemistry Aryl Organic Chemistry Sonogashira coupling Regioselectivity General Medicine Propargyl alcohol Skeleton (computer programming) Biochemistry Aldehyde Catalysis 1-benzofuran chemistry.chemical_compound chemistry Acetylene Drug Discovery Organic chemistry Chromane |
| Zdroj: | Tetrahedron. 63:6015-6034 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2007.02.033 |
| Popis: | The synthesis of a series of aromatic 5,6-benzannelated and naphthyl-benzannelated spiroacetals related to the spiroacetal unit present in the quinonoid antibiotic γ-rubromycin is reported. The key steps include the use of Sonogashira coupling to construct an aryl acetylene that is coupled to an aryl aldehyde forming a propargyl alcohol intermediate. Hydrogenation of the resultant alkynol followed by oxidation produces a masked dihydroxyketone that upon treatment with silica-supported sodium hydrogen sulfate undergoes concomitant deprotection and cyclisation to afford the desired fused aromatic spiroacetal. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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