Synthesis of Polyprionate Derived Natural Products

聚丙酸衍生天然产物的合成

• 批准号: 7246463
• 负责人: JAMES S. PANEK
• 金额: $ 28.18万
• 依托单位: BOSTON UNIVERSITY (CHARLES RIVER CAMPUS)
• 依托单位国家: 美国
• 财政年份: 1998
• 资助国家: 美国
• 起止时间: 1998-05-01 至 2008-06-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/7246463
• 关键词: Alkaloids; Antifungal Agents; Biological Factors; Candida albicans; Chemistry; Complex; Cytotoxic agent; Effectiveness; Facility Construction Funding Category; Goals; Investigation; Libraries; Low Density Lipoprotein Receptor; Methodology; Methods; Nitrogen; Organic Chemistry; Pattern; Pharmaceutical Chemistry; Preparation; Reaction; Reagent; Side; System; Transcription Coactivator; analog; base; callipeltoside A; cytotoxic; leucascandrolide A; novel

DESCRIPTION (provided by applicant): The basis of this proposal seeks the to develop new reaction methods in synthetic organic chemistry, their application to biologically active complex natural products and investigations of fundamental importance in synthetic and medicinal chemistry. This includes efforts to develop new chemistry for the [4 + 2]-annulation of enantioenriched organosilanes. An extensive investigation seeking to evaluate functionalized organosilane reagents for the stereoselective construction of dihydropyrans and tetrahydropyridine ring systems with the eventual goal in their application in synthesis. The enantioselective synthesis of the cytotoxic agent callipeltoside A and the transcription activator of low density lipoprotein receptor will pursued with emphasis on the dihydropyran annulation chemistry. Novel annulation methodology for the stereoselective synthesis of nitrogen bearing heterocycles will be directed at the synthesis of alkaloid 205B. A convergent, enantioselective synthesis of the potent cytotoxic / antifungal agent, leucascandrolide A will be achieved and will suitable for the preparation of side chain analogs with widely diversified substitution patterns. A small focused library of heterocyclic sidechain analogs will be assembled and evaluated for their effectiveness in inhibiting Candida albicans.

描述(申请人提供)：本建议的基础是寻求在合成有机化学中开发新的反应方法，它们在具有生物活性的复杂天然产品中的应用，以及在合成和药物化学中具有基础重要性的研究。这包括努力开发富含对映体的有机硅烷的[4+2]-环化新化学。一项广泛的研究，旨在评估官能化有机硅烷试剂用于二氢吡喃和四氢吡啶环系的立体选择性构建，最终目标是将其应用于合成。细胞毒剂Callipeltoside A和低密度脂蛋白受体转录激活剂的对映选择性合成将着重于二氢吡喃环化化学。 含氮杂环立体选择性合成的新环法将针对生物碱205B的合成。 高效的细胞毒性/抗真菌药物--亮糖内酯A的合成将是一种收敛的、对映体选择性的合成，适合于制备具有多种取代方式的侧链类似物。将组装一个杂环侧链类似物的小型聚焦文库，并评估它们在抑制白色念珠菌方面的有效性。

项目成果

Total synthesis of (+)-SCH 351448.

( )-SCH 351448 的全合成。

• DOI: 10.1021/ol201863b
• 发表时间: 2011
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: Zhu,Kaicheng;Panek,JamesS
• 通讯作者: Panek,JamesS

Sonogashira coupling of functionalized trifloyl oxazoles and thiazoles with terminal alkynes: synthesis of disubstituted heterocycles.

• DOI: 10.1021/ol026099r
• 发表时间: 2002-07
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: N. Langille;L. Dakin;J. Panek

Total synthesis of epothilone A.

• DOI: 10.1021/ol006104w
• 发表时间: 2000
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: Bin Zhu;J. Panek

Total synthesis of rutamycin B and oligomycin C.

• DOI: 10.1021/jo001767c
• 发表时间: 2001-03
• 期刊: The Journal of organic chemistry
• 作者: J. Panek;N. Jain

Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.

• DOI: 10.1021/ol901692n
• 发表时间: 2009-10-01
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: Brawn RA;Panek JS
• 通讯作者: Panek JS