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Total synthesis of Amayllidaceae alkaloids through the highly stereoselective Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone

Submission Date :
9 / 7 / 2007 , 15 : 11 : 54
Abstract Number :
Presenting Type:
Presenting Area :
유기화학 - Development of New Methodologies and Total Synthesis of Bioactive Natural Products
Authors :
한양대학교 화학과,
Assigned Code :
금15D2심 Assigend Code Guideline
Presenting Time :
금 09시 : 55분
The naturally occurring isocarbostryls, narciclasine, lycoricidine and pancratistatin, isolated primarily from the plant genus Amaryllidaceae, have attracted a tremendous attention over the past decades, due in part to their highly potent antitumor activities. trans-Dihydronarciclasine, isolated from the Chinese medicinal plant Zephyranthes candida, is of particular interest as it exhibits even higher potency, 2 to 10-fold, than pancratistatin. Utilizing highly endo-selective Diels-Alder cycloaddition of 3,5-dibromo-2-pyrone with a styrene dienophile, we have achieved the first total synthesis of (±)-trans-dihydronarciclasine in 15.8% total yield over 11 steps. The synthetic steps have been further shortened to 8 steps with the prior incorporation of ester group onto the aromatic ring of the styrene dienophile. We have also found that the above strategy can be readily applied to the total synthesis of galanthamine, the parent member of the galanthamine-type amaryllidaceae alkaloids, isolated from several plants including daffodil bulbs.