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（由申请人提供）：该提案的基础旨在开发合成有机化学中的新反应方法、其在生物活性复杂天然产物中的应用以及在合成和药物化学中具有根本重要性的研究。这包括开发用于对映体富集的有机硅烷的[4 + 2]-环化的新化学的努力。一项广泛的研究旨在评估用于二氢吡喃和四氢吡啶环系统立体选择性构建的官能化有机硅烷试剂，最终目标是在合成中应用。细胞毒性剂 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重点关注二氢吡喃成环化学。 用于立体选择性合成含氮杂环的新型成环方法将针对生物碱 205B 的合成。 将实现强效细胞毒性/抗真菌剂 leucascandrolide A 的收敛、对映选择性合成，并将适用于制备具有广泛多样化取代模式的侧链类似物。将组装一个小型集中杂环侧链类似物库并评估其抑制白色念珠菌的有效性。

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

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

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 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