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以廉价的异香草醛和2,4,6-三羟基苯乙酮为起始原料,经过C-异戊烯基化、选择性甲基化、甲氧甲基化、羟醛缩合、去保护基、催化环化以及脱除甲基等步骤,分别以13.3%和23%的总收率首次完成了天然异戊烯基黄烷酮Glovanon(1)和5-O-methylglovanon(2)的全合成.合成的关键步骤是2,4,6-三羟基苯乙酮的单C-异戊烯基化.所有新化合物的结构都经过1H NMR,IR,MS确认.抑菌活性研究表明,两种新合成的化合物对藤黄微球菌(M.luteus)和大肠杆菌(E.coli)均有良好的抑制作用. 相似文献
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3种香叶基黄烷酮是从毛泡桐(Paulownia tomentosa)水果中分离出的3种具有相似结构的黄酮类化合物。我们以廉价的2,4,6-三羟基苯乙酮,羟基苯甲醛为原料经过取代、氯甲基甲基醚保护、羟醛缩合、分子内的麦克加成反应以及脱甲基甲基醚合成了3个香叶基取代黄烷酮。其结构经过核磁共振氢谱及碳谱(1H NMR,13C NMR)和高分辨质谱(HRMS)等技术手段进行了表征,并采用四氮唑蓝(MTT)法测试了合成化合物对肺癌细胞A459的体外抗肿瘤活性。结果表明,所合成的化合物均具有一定的抗肺癌细胞活性,其中化合物2抗肺癌活性明显优于化合物1和3,其半数抑制浓度为25.6μmol/L,为临床疾病的治疗和药物的研发提供了参考。 相似文献
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以3-羟基苯甲酸为原料,通过中间体(±)-3-羟基-4-甲氧基苯酞合成了(±)-3-正丁基-4-甲氧基苯酞(?)。 相似文献
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以3-甲氧基甲氧基苯甲醛和2,4,6-三甲氧基-3-异戊烯基苯乙酮为原料,经烷基化和缩合反应合成了新化合物——2’-羟基-4-甲氧基-3,4’,6’-三甲氧甲氧基-3’-异戊烯基査尓酮(6);6经环合反应合成了新化合物——(±)-5,7,3’-三甲氧甲氧基-4’-甲氧基-8-异戊烯基黄烷酮(7);7经脱保护和环合反应实现了天然产物(±)-5,7,3’-三羟基-4’-甲氧基-8-异戊烯基-黄烷酮(1,总收率11.6%)和(±)-5,3’-二羟基-7,8-(2,2-二甲基吡喃)-4’-甲氧基黄烷酮(2,总收率10.5%)的全合成,其中1为新化合物,其结构经1H NMR,IR和MS表征。 相似文献
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In this paper we report on a efficient and flexible synthetic route towards the total syntheses of the dihydrocoumarine derivatives hydrangenol (1), phyllodulcin (1a) and macrophyllol (6b). The syntheses started with a readily available phosphonium salt 2 and suitable modified benzaldehydes 3/3a/3b resulting in 46 to 61% overall yields in three to four-steps sequences. The racemic products could be separated by chiral HPLC. The evidence of the (R)-enantiomer for sweetness could be demonstrated for 1a. 相似文献
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The total syntheses of dichroanone and dichroanal B, as well as the formal syntheses of taiwaniaquinol B and taiwaniaquinone D, are reported. 相似文献
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Tsuyoshi Taniguchi 《Tetrahedron》2008,64(37):8773-8779
A total synthesis of (±)-stemonamide and (±)-isostemonamide has been achieved by using a radical cascade that involves two endo-selective cyclizations. (±)-Stemonamine and (±)-isostemonamine are synthesized by chemoselective reduction of (±)-stemonamide and (±)-isostemonamide, respectively. 相似文献
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Concise total syntheses of (±)isopaucifloral F, (±)quadrangularin A, and (±)pallidol, starting from commercially available 3,5-dimethoxybenzoic acid, have been achieved by a sequential process. The overall synthetic strategy involves Nazarov cyclization, Ramberg-Backlund olefination, and Friedel-Crafts alkylation. 相似文献
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A facile approach for the first total synthesis of two naturally occurring geranylated flavonoids, (±)-puyanin 1 and (±)-4′-O-methylbonannione 2 have been obtained with total yield 27% and 21%, respectively. The key steps were regioselective cyclization of geranylated tetrahydroxychalcone and regioselective geranylation of 2, 4, 6-trihydroxy- acetophenone. 相似文献
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Samir Kumar Mandal 《Tetrahedron》2008,64(49):11050-11057
A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon. 相似文献
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Fu-Min Zhang Jian-Dong Liu Xiao-Hui Fan Lei Shi Xiang-Dong Hu Shao-Hua Wang Yong-Qiang Zhang 《Tetrahedron》2006,62(40):9446-9455
A general strategy for synthesizing the crinine-type Amaryllidaceae alkaloids was developed. And total syntheses of four representative crinine-type Amaryllidaceae alkaloids: (±)-haemanthidine, (±)-pretazettine, (±)-tazettine, and (±)-crinamine, were accomplished via a common intermediate 17. This crucial precursor was achieved on the basis of the NBS-promoted semipinacol rearrangement recently developed by our group and an intramolecular Michael addition, which efficiently constructed the sterically congested quaternary carbon center and the hydroindole skeleton of the crinine-type alkaloids, respectively. 相似文献
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Sajal Kanti Mal 《Tetrahedron》2004,60(12):2805-2811
A new approach for a short and efficient synthesis of common cyclohexenone intermediate towards the total synthesis of some furosesquiterpenes and their analogues are described. Regioselective alkylation of Hagemann's ester with 2/3-furyl-2-ethyl bromide followed by hydrolysis cum in situ decarboxylation and 1,4-addition with Gilman's reagent produced the cyclohexanone derivatives which have been utilized for total synthesis of (±) isopallescensin-A, (±) 10-desmethylpallescensin-A, (±) 5-desmethyl-4,5-dehydromicrocionin-1 and (±) isopallescensin-1. 相似文献
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Total synthesis of α-herbertenol, β-herbertenol and 1,13-herbertenediol, employing a Claisen rearrangement and ring-closing metathesis as key reactions for the generation of the cyclopentane containing vicinal quaternary carbons, has been described. 相似文献
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P. Srinivas D. Srinivasa Reddy P.K. Dubey Parthasarathi Das 《Tetrahedron letters》2008,49(42):6084-6086
A new and efficient route to the family of eremophilanes is reported. Key steps are the highly stereocontrolled Diels-Alder reaction and aldol condensation to furnish a cis-decalin system with the desired stereochemistry present in the eremophilane family of natural products. This approach is general and was utilized for the synthesis of (±)-eremophilenolide, (±)-eremophiledinone, and (±)-deoxyeremopetasidione. 相似文献