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Studies on the Total Synthesis of Maistemonine

Author: ChenZhiHua
Tutor: TuYongQiang
School: Lanzhou University
Course: Organic Chemistry
Keywords: Tricyclic compounds Natural Products Tandem Reaction Total synthesis Spectral data Intramolecular New alkaloid Epimers Column chromatographic separation Lewis acid
CLC: R284.1
Type: Master's thesis
Year: 2009
Downloads: 7
Quote: 0
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Abstract


The Stemona alkaloids represent a class of polycyclic alkalodis and widely exist in Stemonaceae plant species. Nowadays, nearly 100 Stemona alkaloids have been isolated, and the total syntheses of them have attracted extensive interests of many chemists due to their relatively complex structures and biological activities. The following two parts are mainly included:1. The isolation of Stemona alkaloids from the nature and the types of them were introduced. Based on their structural characteristics, some representative synthesis works were chosen to be described.2. A TiCl4-promoted tandem Semipinacol/Schmidt reaction has been designed and developed to be a key reaction of the synthesis of stemonamine in our group. For further exploration and extension of our group’s work, the maistemonine with more complicated structures was selected as our synthesis target. During the course of synthetic studies on maistemonine, we used the tandem reation as the key step to construct the pyrrolo[1,2-a]azepine nucleus, and the other three cycles were built by intramolecular Aldol condensation, Dieckmann condensation and Reformatsky reactions respectively. The work is ongoing in our group.

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CLC: > Medicine, health > Chinese Medicine > Of Pharmacy > Traditional Chinese medicine chemical > Chemical analysis and identification
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