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Vinylogous esters and amides: Useful synthons for diversity-oriented and natural product synthesis.

机译：Vinylogous酯和酰胺：有用的合成子，面向多样性和天然产物合成。

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The first total synthesis of boehmeriasin A was achieved in seven steps from readily available materials with an overall yield of 29%. The absolute stereochemistry of the natural product was determined to be of the (R)-configuration. (-)-(R)-Boehmeriasin A demonstrated potent cytotoxicity in several cancer cell lines including drug resistant cancer cells where paclitaxel is inactive.;An efficient and mild method for the construction if chromones was developed that requires only a single purification step at the end of the sequence and results in moderate to good yields of the isolated chromones. This method was applied toward the synthesis of 5-hydroxy-2-(2-phenylethyl)chromone, a neuroprotective chromone.;The reduction of tertiary amides using Cp2Zr(H)Cl to the corresponding aldehydes on a preparatory scale results in good isolated yields of the products. Through a modified workup procedure, issues not previously observed were overcome to afford good isolated yields of the corresponding aldehydes.

机译：从易于获得的材料中以七个步骤完成了勃姆球菌素A的第一次全合成，总收率为29％。天然产物的绝对立体化学被确定为（R）-构型。（-）-（R）-Boehmeriasin A在包括紫杉醇不活泼的耐药性癌细胞在内的多种癌细胞系中显示出强的细胞毒性;如果开发了色酮，则仅需一个纯化步骤即可构建一种高效温和的方法序列的末端并产生中等至良好产率的分离的色酮。该方法用于合成神经保护性色酮5-羟基-2-（2-苯乙基）色酮。;使用Cp2Zr（H）Cl在制备规模上将叔酰胺还原为相应的醛可得到良好的分离收率产品。通过改进的后处理程序，克服了以前未曾观察到的问题，从而获得了相应的醛类，其分离产率高。

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作者
Leighty, Matthew W.;
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作者单位

University of Kansas.;

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授予单位 University of Kansas.;
学科 Chemistry Organic.
学位 Ph.D.
年度 2009
页码 157 p.
总页数 157
原文格式 PDF
正文语种 eng
中图分类有机化学;
关键词
入库时间 2022-08-17 11:38:27

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1. Studies toward nitrogen-containing natural products using radical cyclizations of chiral vinylogous amides [J] . Cordes M, Franke D Synlett . 2004,第11期

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4. Synthesis of Natural and Unnatural Products from Sugar Synthons [C] . Minoru Isobe, Yoshiyasu Ichikawa American Chemical Society . 2003

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5. Synthesis of N-acyl vinylogous urea-containing natural products and development and applications of zirconium(IV)-catalyzed ester -amide exchange [D] . Han, Chong 2008

机译：含N-乙烯基乙烯基脲的天然产物的合成及锆（IV）催化的酯-酰胺交换的开发与应用
6. Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides [O] . Ming Chen, John F. Hartwig -1

机译：铱催化从乙烯基酯和酰胺中烯醇硅烷的对映体选择性烯丙基取代
7. TRICYCLO3.3.0.02,8OCTANONES AS BUILDING BLOCKS IN NATURAL PRODUCTS SYNTHESIS. –SYNTHESIS OF (±)-FORSYTHIDE AGLYCON DIMETHYL ESTER– [O] . Tadahiro Takemoto, Sachihiko Isoe 1982

机译：Tricyclo 3.3.0.02,8辛烷值是天然产品合成中的构建块。 - 对（±）的合成 - 乙酰甘胺二甲酯 -

Vinylogous esters and amides: Useful synthons for diversity-oriented and natural product synthesis.

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