Total Synthesis of (−)-(2R)-Dihydromyricoidine
| Autor: | Ursula A. Häusermann, Manfred Hesse, Anthony Linden, Jiangao Song |
|---|---|
| Rok vydání: | 1996 |
| Předmět: |
Natural product
Stereochemistry Organic Chemistry Absolute configuration Enantioselective synthesis Total synthesis Biochemistry Catalysis Inorganic Chemistry Spermidine chemistry.chemical_compound chemistry Drug Discovery Wittig reaction Michael reaction Specific rotation Physical and Theoretical Chemistry |
| Zdroj: | Helvetica Chimica Acta. 79:1995-2003 |
| ISSN: | 0018-019X |
| DOI: | 10.1002/hlca.19960790721 |
| Popis: | An asymmetric synthesis of the spermidine alkaloid (−)-(2R)-dihydromyricoidine (5) was performed by employing two ring-enlargement reactions. The chiral center was introduced by a diastereoselective Michael addition of perhydropyridazine (7) to the α,β-unsaturated ester 6. The (Z)-CC bond was obtained by a selective Wittig reaction. The synthetic compound 5 was found to have a negative value for the specific rotation. This is in contrast to that of the natural product reported in the literature. Therefore, as an outcome of this synthesis, the absolute configuration of the natural alkaloid should be inverted to be as shown in structure V. |
| Databáze: | OpenAIRE |
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