首页> 外文学位 >Part I. Novel analogs of the natural hormone alpha,25-dihydroxyvitamin D(3): Design, synthesis and biological evaluation. Part II. New silicon-mediated ring expansions of n-sized 2-cycloalkenones into homoallylic n+3 and hydroxyolefinic n+3+m medium sized lactones: Total synthesis of (+)-cis-lauthisan and (-)-phoracantholide-J.

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Part I. Novel analogs of the natural hormone alpha,25-dihydroxyvitamin D(3): Design, synthesis and biological evaluation. Part II. New silicon-mediated ring expansions of n-sized 2-cycloalkenones into homoallylic n+3 and hydroxyolefinic n+3+m medium sized lactones: Total synthesis of (+)-cis-lauthisan and (-)-phoracantholide-J.

机译：第一部分。天然激素α，25-二羟基维生素D（3）的新型类似物：设计，合成和生物学评估。第二部分n尺寸的2-环烯酮新的硅介导的环扩展成中等烯丙基n + 3和羟基烯属n + 3 + m中等尺寸的内酯：（+）-顺-月桂聚糖和（-）-紫杉醇-J的全合成。

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Part I. Novel analogs of the natural hormone 1alpha,25-dihydroxyvitamin D3: design, synthesis and biological evaluation. The natural hormone 1alpha,25-dihydroxyvitamin D3 (calcitriol) is known to be involved in a number of different biological responses including calcium homeostasis, cell proliferation and differentiation as well as regulation of gene transcription. In an effort to develop efficacious chemotherapeutic drugs for a variety of human diseases, we have designed and synthesized a variety of novel vitamin D3 related analogs. A series of analogs, combining both the non-calcemic 1-hydroxymethyl-A-ring and 19-nor-A-ring modification with a known potentiating C,D-ring side-chain, were synthesized from a novel 19-nor-1-hydroxymethyl A-ring phosphine oxide. These hybrid analogs were shown to be equal to or greater in antiproliferative activity with respect to calcitriol in our standard murine keratinocyte in vitro assays. Studies determining the calcemic responses of these analogs are ongoing.; Part II. New silicon-mediated ring expansions of n-sized 2-cycloalkenones into homoallylic n+3 and hydroxyolefinic n+3+m medium sized lactones: total synthesis of (+)-cis-lauthisan and (-)-phoracantholide-J. Several 8-10-membered ring cis-homoallylic lactones have been prepared from 2-cycloalkenones using a novel silicon and hypervalent iodine-mediated n+3 ring expansion methodology. n+3+m ring expansions of lactones containing O-silyl protected tethers gave access to larger lactone ring systems. Using chiral epoxides, the total synthesis of both (+)-cis-lauthisan and (-)-phoracantholide-J has been completed.

机译：第一部分：天然激素1alpha，25-dihydroxyvitamin D3的新型类似物：设计，合成和生物学评估。已知天然激素1alpha，25-dihydroxyvitamin D3（calcitriol）参与许多不同的生物学反应，包括钙稳态，细胞增殖和分化以及基因转录的调控。为了开发针对多种人类疾病的有效化学治疗药物，我们设计并合成了多种新型维生素D3相关类似物。由新型19-nor-1合成了一系列类似物，它们将非钙化的1-羟甲基A-环和19-nor-A-环修饰与已知的增强C，D-环侧链结合在一起-羟甲基A环氧化膦。在我们的标准鼠类角质形成细胞体外试验中，这些杂合类似物对骨化三醇的抗增殖活性相等或更高。确定这些类似物的钙减少反应的研究正在进行中。第二部分n尺寸的2-环烯酮新的硅介导的环扩展成中等烯丙基n + 3和羟基烯属n + 3 + m中等尺寸的内酯：（+）-顺-月桂聚糖和（-）-紫杉醇-J的全合成。使用新颖的硅和高价碘介导的n + 3环膨胀方法，已经由2-环烯酮制备了几种8-10元环顺式-烯丙基内酯。含有O-甲硅烷基保护的链的内酯的n + 3 + m环扩展使得可以进入更大的内酯环系统。使用手性环氧化物，已经完成了（+）-顺式-月桂聚糖和（-）-菲酰胺-J的全合成。

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作者
Hatcher, Mark Andrew.;
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作者单位

The Johns Hopkins University.;

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授予单位 The Johns Hopkins University.;
学科 Chemistry Organic.
学位 Ph.D.
年度 2006
页码 193 p.
总页数 193
原文格式 PDF
正文语种 eng
中图分类有机化学;
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外文文献

1. New silicon-mediated, sequential ring expansions of n-sized 2-cycloalkenones into hydroxyolefinic n+m+p medium-sized lactones: Short synthesis of (-)-phoracantholide-J [J] . Posner GH, Hatcher MA, Maio WA Organic letters . 2005,第19期

机译：新的硅介导的，n尺寸的2-环烯酮的连续环扩环成羟基烯烃n + m + p中等尺寸的内酯：（-）-phorantantide-J的短合成
2. New silicon-mediated ring expansion of n-sized conjugated cycloalkenones into homoallylic n+3 lactones [J] . Mark A.Hatcher, Kristina Borstnik, Gary H.Posner Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2003,第29期

机译：n尺寸共轭环烯酮新的硅介导的扩环成均烯丙基n + 3内酯
3. New synthetic methodology for ring expansion of n-sized conjugated cycloalkenones into homoallylic n+3 lactones:three-step synthesis of fragrant phoracantholide [J] . Gary H.Posner, Qiang Wang, Bethany A.Halford, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2000,第49期

机译：n尺寸共轭环烯酮扩环成均烯丙基n + 3内酯的新合成方法：香型菲的三步合成
4. Studies in synthetic organic chemistry: Part I. The synthesis of novel antimalarial artmeisinin dimers. Part II. Electronically stabilized versions of antimalarial acetal trioxanes. Part III. Novel analogs of natural hormone 1-alpha, 25-dihdroxyvitamin D3: Design, synthesis and biological evaluation of CYP24 inhibitors. Part IV. New silicon mediated ring expansions of N-sized 2-cycloalkenones into homoallylic N+3 sized lactones. [D] . Kalinda, Alvin Solomon. 2009

机译：合成有机化学研究：第一部分。新型抗疟药青蒿素二聚体的合成。第二部分电子稳定版的抗疟缩醛三恶烷。第三部分天然激素1-α，25-二羟维生素D3的新型类似物：CYP24抑制剂的设计，合成和生物学评估。第四部分新的硅介导的N尺寸的2-环烯酮的环扩环成均烯丙基N + 3尺寸的内酯。
5. New Silicon-Mediated, Sequential Ring Expansions of n-Sized 2-Cycloalkenones into Hydroxyolefinic n + m + p Medium-Sized Lactones: Short Synthesis of (-)-Phoracantholide-J [O] . -1

机译：N新的硅介导，序列环膨胀，N型2-环烯酮进入羟基烯烃N + M + P中等薄膜：短合成（ - ） - PhoracantHolide-J.

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