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Synthesis of indole- rigid ring the alkaloids Swainsonine and ring the peptide lactone Thalassospiramides molecules

Author: WangXiaoLing
Tutor: LinGuoQiang；WeiBangGuo
School: Fudan University
Course: Chemical Biology
Keywords: Asymmetric Synthesis Natural Products Alkaloid Swainsonine Thalassospiramides
CLC: R284
Type: Master's thesis
Year: 2011
Downloads: 70
Quote: 0
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Abstract


The synthesis of natural products is the field of cross-over study in natural product chemistry and synthetic organic chemistry, is the driving force for the development of organic synthesis methodologies and strategies, is an important way to find new reactions, new reagents, new methods, new theories. Structural modification of natural products, transformation and structure-activity relationship studies is reasonable, safe and effective use of natural products direct way, is also an important source of new drug discovery. Multi-hydroxy indole (pyrrole) alkaloids are an important class of nitrogen-containing heterocyclic alkaloids are widespread in nature. Since the vast majority of such alkaloids have a wide range of biological activity and chemical structure, in recent years, many synthetic organic chemist and pharmaceutical scientists favor. For example, isolated from the fungus Rhizoctonia leguminicola an important class of anticancer activity and immune-enhancing activity of multi-hydroxy indole the alkaloids Swainsonine its isomers in the past 30 years has aroused extensive research. Marine natural products research has become one of the hot spots for nearly half a century of natural product chemistry research. Due to the activity of the marine natural products is broader, more complex structure, and a very low content of relying on separate means to obtain marine natural products can not meet the further research needs pharmacology. Thus, the asymmetric synthesis of marine natural products have become one of the most important content of organic synthetic chemistry research. Natural product analogs, key intermediates and analysis methods, the paper carried out the research work, mainly to obtain the following results: First, the papers in the group established to 2-64 on the basis of the glutamate Preparation of synthetic block, Step 6 prepared by the reaction of ketones 2-80, the development of Li (t-BuO) 3A1H as reductant to its high selectively reduced to the alcohol 2-81 The method of (dr = 95:5), and then transformed through the literature similar methods, completion of the synthesis of (-)-8a-epi-Swainsonine asymmetric. A important activity of multi-hydroxy indole alkaloids and their analogues asymmetric synthesis of new method based on cheap glutamate synthesis. Secondly, the establishment of a synthesis method for the synthesis of marine natural products Thalassospiramides A and B the skeleton rings in three key segments. The cyclopeptide the lactone Thalassospiramides A and B Fenical et al 2006 the marine discharge lines bacteria Thalassospir separation to get an anti-inflammatory activity of secondary metabolites, because of its complex structure, in particular a rigid class molecules containing very strong 12-membered ring the peptide lactone skeleton structure, synthesis more difficult. The concrete realization tyrosine amino selective methylation reaction, the preparation of a high yield of compound 3-16 was obtained; established a synthetic method of the hydroxymethyl aminoalcohol trans double bond fragment 3-37; studied better connection between each fragment condensation conditions; explore the the marine natural products Thalassospiramides A and B molecules in the rigid ring 3-41 ring conditions. These work laid the foundation for the group to continue its asymmetric synthesis of such molecules and activity evaluation study.

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