Strategy towards the enantioselective synthesis of schiglautone A
| Autor: | Camille Le Chapelain |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Ketone Molecular Structure 010405 organic chemistry Stereochemistry Organic Chemistry Diastereomer Enantioselective synthesis Stereoisomerism 010402 general chemistry 01 natural sciences Biochemistry Aldehyde Triterpenes 0104 chemical sciences Cyclopropane Stereocenter chemistry.chemical_compound Aldol reaction chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic & Biomolecular Chemistry, 15 (29) |
| ISSN: | 1477-0539 |
| Popis: | Herein is described a convergent enantioselective route to an advanced intermediate in the synthesis of schiglautone A, a Schisandra triterpenoid with an unusual architecture. The synthetic route to this intermediate displaying 6 of the 7 stereocenters builds upon two fragments, an aldehyde elaborated from the Wieland–Miescher ketone, and a ketone. The preparation of the latter features a lithiation–borylation enzymatic resolution sequence, which led to the formation of the desired product with high enantio- and diastereoselectivities. After aldol coupling of the two fragments, the final quaternary stereocenter was installed by cyclopropane opening. The functionalized intermediate was isolated as a single diastereoisomer and thus offers a valuable starting point for further synthetic exploration. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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