Asymmetric Synthesis of the Oxygenated Polycyclic System of (+)-Harringtonolide
| Autor: | Hajer Abdelkafi, Patrick Herson, Bastien Nay |
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| Rok vydání: | 2012 |
| Předmět: |
Models
Molecular Harringtonines Molecular Structure Stereochemistry Organic Chemistry Cyclohexene Enantioselective synthesis Stereoisomerism Metathesis Ring (chemistry) Biochemistry chemistry.chemical_compound chemistry Cyclization Surface modification Stereoselectivity Physical and Theoretical Chemistry Oxidation-Reduction Harringtonolide |
| Zdroj: | Organic Letters. 14:1270-1273 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol300133x |
| Popis: | A straightforward asymmetric synthesis of the cage oxygenated structure of (+)-harringtonolide has been accomplished for the first time. The key steps involved (i) a templated stereoselective IMDA reaction to build a highly functionalized cyclohexene ring D, (ii) functionalization of the cycloadduct, (iii) ring-closing metathesis providing the five-membered ring C, and finally (iv) a challenging one-step cascade cyclization of an epoxy-alcohol toward the target structure, whose mechanism was investigated. |
| Databáze: | OpenAIRE |
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