Synthesis of (+)-Omphadiol and (+)-Pyxidatol C
| Autor: | Gowrisankar Parthasarathy, Markus Kalesse, Ulrike Eggert |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Cyclopropanation Stereochemistry Organic Chemistry Epoxide Alcohol Protonation 010402 general chemistry Metathesis 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Oxidation state Physical and Theoretical Chemistry Cyclopentane |
| Zdroj: | Organic letters. 18(9) |
| ISSN: | 1523-7052 |
| Popis: | The synthesis of (+)-omphadiol and (+)-pyxidatol C was achieved through two independent strategies. For the synthesis of (+)-omphadiol, dicyclopentadienone was used as the workbench on which the three contiguous stereocenters of the cyclopentane could be introduced selectively. These include a tertiary alcohol and a selective protonation of an enolate. A ring-closing metathesis and a cyclopropanation concluded the synthesis. For the synthesis of pyxidatol C, we used the epoxide derived from (R)-linalool that was transformed to cyclopentane 23. After chain extension, another ring-closing metathesis followed by oxidation state changes and finally a cyclopropanation led to (+)-pyxidatol C. |
| Databáze: | OpenAIRE |
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