Synthetic Studies toward (+)-Paniculatine
碩士 === 國立中興大學 === 化學系所 === 97 === (+)-Paniculatine having a tetracyclic framework is produced through stereocontrolled coupling of (R)-pulegone-derived (R)-5-methyl-2-cyclohexenone with Zn-Cu reagent derived from methyl 3-iodopropanate, base-promoted intramolecular cyclization, regiocontrolled C-alk...
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| Format: | Others |
| Language: | zh-TW |
| Online Access: | http://ndltd.ncl.edu.tw/handle/72890699118344256007 |
| Summary: | 碩士 === 國立中興大學 === 化學系所 === 97 === (+)-Paniculatine having a tetracyclic framework is produced through stereocontrolled coupling of (R)-pulegone-derived (R)-5-methyl-2-cyclohexenone with Zn-Cu reagent derived from methyl 3-iodopropanate, base-promoted intramolecular cyclization, regiocontrolled C-alkylation of diketone enolate with 3-bromomethyl-N-Boc-tetrahydropyridine, chemoselective enolization, and Pd-mediated intramolecular coupling of enol triflate with alkene. The requisite controlled reduction of ketone with NaBH4/CeCl3 followed by monoepoxidation of diene with DCC/UHP (urea hydrogenperoxide) provided diene monoepoxide intermediate. Further efforts direct toward elaboration of monoepoxide intermediate into (+)-Paniculatine .
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