Toward the Total Synthesis of Hygrocin B and Divergolide C: Construction of the Naphthoquinone–Azepinone Core
| Autor: | Christopher C. Nawrat, Russell R. A. Kitson, Christopher J. Moody |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Biological Products
Alkylation Molecular Structure Lactams Macrocyclic Organic Chemistry Regioselectivity Total synthesis Stereoisomerism Core (manufacturing) Azepines Oxime Biochemistry Combinatorial chemistry Naphthoquinone chemistry.chemical_compound chemistry Oximes Beckmann rearrangement Benzoquinones Tetralone Organic chemistry Macrolides Physical and Theoretical Chemistry Naphthoquinones |
| Zdroj: | Organic Letters. 16:1896-1899 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A highly regioselective Diels-Alder approach toward the bioactive natural products hygrocin B and divergolide C is presented. The route uses an unusual benzoquinone-azepinone dienophile prepared in 8 steps from ethyl 8-methoxy-1-naphthoate, by a route which includes, as key steps, a Birch alkylation and a Beckmann rearrangement of a tetralone oxime, both of which are demonstrated on multigram scale. The naphthoquinone-azepinone core is suitably functionalized for addition of the ansa-chain, found in the natural products. |
| Databáze: | OpenAIRE |
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