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Construction of 6/6-Bicyclic Lactones Via Microwave-Assisted Tandem Reactions and Synthesis of Isoindolin-1-ones

Author: JiangXiuQing
Tutor: DaiWeiMin；WuJinLong
School: Zhejiang University
Course: Organic Chemistry
Keywords: Microwave-assisted Intramolecular Diels-Alder reaction Series wittig-IMDA reaction 6/6- and macrolide Hydrogenated iso- indol-1 - one Oxa -Diels-Alder reaction
CLC: TQ25
Type: Master's thesis
Year: 2010
Downloads: 17
Quote: 0
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Abstract


The intramolecular Diels-Alder reaction as an extremely important class of organic reactions , and can efficiently form a carbon -carbon bond , is a powerful means to build a multi-membered ring complex structures . This thesis involving microwave-assisted tandem Wittig and intramolecular Diels-Alder ( IMDA) reaction for the preparation of 6/6- macrolide compounds IMDA reaction for the Cytochalasin Z8 hydrogenation isoindol-1 - one skeleton synthesis. The first chapter of this thesis, is the background of the intramolecular Diels-Alder reaction . We first introduced by the IMDA reaction formation 5/6- and macrolide , 6/6- and ring lactone and lactam structure and stereochemistry of compounds , and then describes the Lewis acid catalyzed the IMDA reaction build 6 / 6 - and macrolide reported. Meanwhile, lists some of the far IMDA reaction to construct an example of a natural product containing 6/6- and macrolide . Microwave-assisted organic synthesis and known \Detailed discussion of the ester group connected 1,3,9 - decatrienyl preparation of raw materials , the microwave -assisted IMDA reaction for the preparation of 6/6- and macrolide compounds . To determine the stereochemistry of the product through the literature and single crystal diffraction results . Thereafter, the bromo compound , PPh3 and aldehydes as substrates, and the alkali catalyst , the use of microwave - assisted concatenate the Wittig reaction and IMDA , synthesized by a series of 6/6- and ring ester compound , and using 1,3 9 - decatrienyl microwave-assisted IMDA reaction to compounds belonging, using single-crystal diffraction results to determine the compounds of the three-dimensional structure . Discussed in the third chapter of the thesis hexahydro isoindolone structure of natural products cytochalasins, analysis and inverse synthetic compounds cytochalasin Z8 . Wittig reaction , and the IMDA reaction through the aqueous phase , the initial completion the cytochalasins Z8 hydrogenated isoindol -1 - Synthesis of ketone fragment skeleton . Synthetic route to explore the process , we found that a class of oxygen hetero-Diels-Alder reaction , the carbon and oxygen heterocyclic ring-opening of a new class of compounds using p-toluenesulfonic acid as a catalyst . The last part of the paper lists the main experimental step , the structure of the compound characterization data , references , the main compound of the 1H and 13C NMR spectra as well as X -ray single crystal diffraction parse the data and so on.

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