Diastereoselective Synthesis of Cephalotaxus Esters via Asymmetric Mukaiyama Aldol Reaction
| Autor: | Wei-Dong Z. Li, Guo-Zhen Ma, Lu Liu, Pengfei Li, Li Chen |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
biology
Silylation 010405 organic chemistry Stereochemistry Organic Chemistry Acetal Ketene Cephalotaxus 010402 general chemistry biology.organism_classification 01 natural sciences Biochemistry 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Aldol reaction Side chain Organic chemistry Stereoselectivity Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 19(9) |
| ISSN: | 1523-7052 |
| Popis: | We report a protocol for efficient stereoselective installation of the chiral oxygen-containing tetrasubstituted tertiary carbon stereocenter of the side chain of cephalotaxus esters by means of highly diastereoselective Mukaiyama aldol reactions between α-keto esters (2) and a (Z)-α-chloro ketene silyl acetal. This protocol permitted synthesis of cephalotaxus esters including six natural products in good to excellent yields (up to 94%) with high diastereoselectivities (dr up to 97:3) and could be performed on a multigram scale. |
| Databáze: | OpenAIRE |
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