Electrophilic C12 Building Blocks for Alkaloids: Formal Total Synthesis of (±)-Maritidine
| Autor: | C Roe, GR Stephenson |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
Plants
Medicinal Molecular Structure Stereochemistry Organic Chemistry Substituent Total synthesis Stereoisomerism Heterocyclic Compounds 4 or More Rings Biochemistry chemistry.chemical_compound Nucleophile chemistry Cyclohexenone Benzyl alcohol Electrophile Amaryllidaceae Alkaloids Physical and Theoretical Chemistry Maritidine |
| Zdroj: | Organic Letters. 10:189-192 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | Silyl-protected benzyl alcohol derivatives and the salt 1 are used to form ortho-substituted C-12 electrophilic organoiron building blocks which are converted into a spirocyclic cyclohexenone to complete a formal total synthesis of (+/-)-maritidine (5). The choice of TBDPS protection was shown to be better than TIPS and compatible with ipso nucleophile addition to form a quaternary center. The reaction sequence is the first example of a successful application in the synthesis of an arylcyclohexadienyliron complex with an ortho-carbon substituent in the position required for Amaryllidaceae alkaloids of this type. |
| Databáze: | OpenAIRE |
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