Synthetic studies on functionalized chiral cyclopentanones

• Main Author: 黃俊傑
• Other Authors: Minoru Isobe
• Format: Others
• Language: en_US
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/31258556814380987325

碩士 === 國立清華大學 === 化學系 === 101 === In this thesis, we focused our attention on constructing the chiral cyclopentanone skeleton of PGE2 through heteroatom-directed conjugate addition and cyclization (HADCAC). The synthetic routes includes: (1) The (R)-configuration alcohol (R)-109 was established from Evans asymmetric aldol reaction by the boron enolate of (R)-oxazolidinone 107 and the vinylsulfone aldehyde 96. (2) The absolute configuration of the secondary alcohol (R)-109 was confirmed by the modified Mosher’s method. (3) The chiral cyclopentanone (R)-112 was obtained from HADCAC of oct-1-ynyllithium to the oxazolidinone (R)-109, but the result of the vinyl nucleophile was failed. (4) The Weinreb amide (R)-129 was implemented from the oxazolidinone (R)-109 for improvement of HADCAC. (5) The chiral cyclopentanone (R)-127 was obtained from the HADCAC of the vinyl zincate to the Weinreb amide (R)-129.