兰州大学机构库 >化学化工学院
(-)-Cladospolide B的全合成研究,Chloriolide和Isocladosporin的合成研究
其他题名Asymmetric Total Synthesis of (-)-Cladospolide B, Syntheses on Chloriolide and Isocladosporin
王文宽
导师厍学功
学位类别博士
2010-05-29
关键词大环内酯 Mitsunobu反应 三组分Lichpin反应 syn-二取代的四氢吡喃环 Sharpless不对称环氧化 Sharpless不对称双羟化 BiBr3 RCM
中文摘要本论文对十二元环大环内酯类天然产物(-)-Cladospolide B进行了不对称全合成研究,同时还对天然产物Chloriolide和Isocladosporin进行了合成探索。包括下面四个部分: 一、天然产物(-)-Cladospolide B的不对称全合成研究 简要介绍了其它小组对(-)-Cladospolide B的合成工作。 以廉价易得的(S)-乳酸乙酯和1,5-戊二醇为起始原料,以Sharpless不对称双羟化、Mitsunobu、RCM等反应为关键步骤构建了该分子骨架,经14步化学转化以3.7%的总收率简洁高效地完成了(-)-Cladospolide B的不对称全合成。 二、 十二元环大环内酯类天然产物Chloriolide的不对称合成研究 简要介绍了其它小组对Chloriolide的合成工作。 尝试了不同策略来合成Chloriolide。最后,我们以三组分的Lichpin、Sharpless 不对称环氧化、CBS还原以及Payne反应为关键步骤,得到了关键中间体,这对Chloriolide的进一步研究奠定了基础。目前的研究工作正在进行中。 三、 天然产物Isocladosporin的不对称合成研究 尝试了不同的策略来合成Isocladosporin。最后,我们通过BiBr3催化的环化反应构筑了syn-二取代的四氢吡喃环,并以三组分Lichpin反应为关键步骤得到了关键中间体。对Isocladosporin的研究正在进行中。 四、Nazarov环化及其在天然产物合成中的应用(综述) 对Nazarov环化的机理,影响环化反应活性的因素,顺旋环化中旋转方向的控制,酸的作用,生成双键位置控制,Nazarov环化的中断以及该反应在天然产物合成中的应用作了简要的综述。
英文摘要This dissertation described the asymmetric syntheses of natural products (-)-Cladospolide B, Chloriolide and Isocladosporin. It consisted of the following four parts: Chapter 1. Asymmetric total synthesis of natural product (-)-Cladospolide B The work of other groups in synthsis of (-)-Cladospolide B was briefly introduced. The natural product (-)-Cladospolide B was synthesized in 14 steps from commerically available (S)-ethyl lactate and 1, 5-pentanediol, in which Sharpless asymmetric dihydroxylation, Mitsunobu esterification, Ring closing metathesis were the key steps and two stereocenters were established facilely with highly selectivity. Chapter 2. Studies on asymmetric synthesis of natrual product Chloriolide The work of other group in synthsis of Chloriolide was briefly introduced. various synthetic strategies to synthesize Chloriolide were tested. Asymmetric synthesis of Chloriolid was performanced using three-componment Lichpin, Sharpless asymmetric epoxidation, CBS-reduction and Payne reactions as the key steps, in which the key intemediates were obtained. Further study on total synthesis of Chloriolide is ongoing. Chapter 3. Studies on asymmetric synthesis of natrual product Isocladosporin Various synthetic strategies have been tested to synthesize Isocladosporin. The syn-disubstituted pyran was constructed by ring closure catalized by BiBr3. The key intermediate was obtained through three-compoment Lichpin reaction as the key step. Further study on total synthesis of Isocladosporin is ongoing. Chapter 4. Nazarov cyclization and the applications in natural products syntheses (review) The mechanism of Nazarov cyclization, factors influencing activity, control of torquoselectivity in conrotatory cyclization, function of acid, localizing the double bond in the product, interrupted Nazarov cyclization pathways, and its applications in total synthesis of natural products were briefly introduced.
全文链接查看原文
授予单位兰州大学
授予地点兰州
语种中文
文献类型学位论文
条目标识符http://ir.lzu.edu.cn/handle/262010/238708
Collection化学化工学院
Recommended Citation:
GB/T 7714
王文宽. (-)-Cladospolide B的全合成研究,Chloriolide和Isocladosporin的合成研究[D]. 兰州. 兰州大学,2010.
Files in This Item:
There are no files associated with this item.
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Altmetrics Score
谷歌学术
谷歌学术Similar articles in Google Scholar
[王文宽]'s Articles
百度学术
百度学术Similar articles in Google Scholar
[王文宽]'s Articles
必应学术
必应学术Similar articles in Google Scholar
[王文宽]'s Articles
Related Copyright Policies
Null
???item.sidebar.baidu.bookmark-share???
???jsp.display-item.all??? (0)
[???jsp.display-item.idea???]
???jsp.display-item.comment-text2???
Items in IR are protected by copyright, with all rights reserved, unless otherwise indicated.