17-Hydroxymandarone B 合成之進展;Progress in the Synthesis of 17-Hydroxymandarone B

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/89240

Title:	17-Hydroxymandarone B 合成之進展;Progress in the Synthesis of 17-Hydroxymandarone B
Authors:	彭御鈞;Peng, Yu-Chun
Contributors:	化學學系
Keywords:	掌性輔助劑;脱氫松香胺;夫-夸醯化反應
Date:	2022-09-29
Issue Date:	2022-10-04 11:02:04 (UTC+8)
Publisher:	國立中央大學
Abstract:	本篇論文的目標為合成天然物17-Hydroxymandarone B。在此合成中，我們簡化了之前的合成步驟，使得合成前驅物11更有效率。另外在本合成中有一氫化反應會形成非鏡像異構物的混合物，化合物13。但此非鏡像異構物的混合物無法藉由管柱層析分離，使的本合成無法得到單一組態的17-Hydroxymandarone B。我們發現將混合物14與掌性輔助劑反應後，所得之非鏡像異構物的混合物可以藉由管柱層析有效分離。得到與天然物17-Hydroxymandarone B立體中心相同的中間物，並繼續進行天然物17-Hydroxymandarone B的合成研究。 ;The natural product 17-Hydroxymandarone B is the target molecular in this thesis. In this synthesis, we simplified the previous synthetic steps and made the synthesis of compound 11 more efficient. In addition, a hydrogenation reaction in this synthesis formed a mixture of diastereoisomers. However, the mixture of diastereomers could not be separated by column chromatography, so pure 17-Hydroxymandarone B could not be obtained in the end. We found that by reacting the above mixture with a chiral auxiliary, the resulting diastereoisomers were efficiently separated by column chromatography. The intermediate possesses the same stereocenters with the natural 17-Hydroxymandarone B, and the synthesis of the natural 17-Hydroxymandarone B could be continued.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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