兰州大学机构库 >化学化工学院
(–)-Heliconol A、Kawain 类、二氢异香豆素类及脱碳木脂素类化合物的全合成研究
其他题名Studies on the Total Synthesis of (–)-Heliconol A, Kawain, Isochroman and Norlignans Compounds
权伟国
导师潘鑫复 ; 厍学功
学位类别博士
2007-05-01
关键词天然产物 全合成
中文摘要

本文完成了四个天然产物、六个天然产物异构体及四个天然产物前体的全合成研究,其中两个天然产物为首次全合成。共包括以下五个部分:

一、Prins 环化反应的研究进展 (综述)
综述了近年来 Prins 成环反应的一些新的研究进展,以及其在天然产物全合成中的应用。

二、二氢异香豆素类化合物的全合成研究
简要介绍了二氢异香豆素类天然产物的相关生理活性,及合成研究报道。并以4-丁基-3,5-二甲氧基苯甲醛为起始原料,用Sharpless不对称双羟化反应作为关键步骤,合成了手性的7-butyl-6,8-dihydroxy-3(R)-pentylisochroman-1-one(2-9) 又用一 线 7-Butyl-6,8-dihydroxy-3-pent-11-enylisochroman
-1-one((±)2-10)
的消旋体的合成。

三、(–)-Heliconol A 的首次全合成研究
简要介绍了 Heliconol A 类天然产物的相关生理活性。以 2-(苄氧基甲基)环戊烯酮为起始原料,以 CBS 不对称还原为关键步骤,通过两次诱导的高选择性双羟化反应等步骤完成了(–)-Heliconol A(3-1)及它的一个异构体(3-18)的首次全合成。

四、两个 kawain 类天然产物全合成研究
简要介绍了 kawain 类天然产物的生理活性,及合成研究报道。以醛和手性丙二 (+)-Dihydrokawain (4-1a) (+)-Dihydrokawain-5-ol (4-2a)在内的所有对映体(4-1b, 4-2b, 4-3a 4-3b)的合成。

五、脱碳木脂素的手性全合成研究
简要介绍了脱碳木脂素类天然产物的分布及相关生理活性及合成研究报道。并设计了以(S,S)-1,4-二苄氧基-2,3- 环氧丁烷为起始原料,成功地合成了Agatharesino(5-1b) Sugirresinol(5-2b)二甲醚化合物,首次合成了 Nyasol (5-4b)的二甲醚及 Tetrahydronysol(5-5),并且验证了它们的立体结构。

英文摘要

This thesis main focused on the total syntheses of several natural products. Include thefollowing five parts:

Chapter 1. The recent progress on the study of the Prins Cyclization (review)
The review introduced some methods on recently study of the Prins Cyclization, and which were applied in the synthesis of natural products.

Chapter 2. The first total synthesis of 7-butyl-6, 8-dihydroxy-3(R)-pentylisochroman-1-one The definition, classification of isochroman comounds, and previous synthetic reports of them were introduced briefly. A novel approach has been found and the first total synthesis of 7-butyl-6,8-dihydroxy-3(R)-pentylisochroman-1-one was accomplished.In which Sharpless asymmetric dihydroxylation was the key step

Chapter 3. The first total synthesis of (–)-Heliconol A and its diastereoisomer The definition of heliconol A compounds were introduced in brief. A facile total synthesis of the (–)-Heliconol A as well as its diastereoisomer is described, in which different reaction sequences lead to different results. If osmylation followed hydrolysis afforded a
single isomer, otherwise, afforded a mixture of (–)-Heliconol A and its diastereoisomer 3-18. Other important processes include the catalytic asymmetric CBS reduction and induced highly stereoselective osmylation.

 

Chapter 4. Enantioselective synthesis of all stereoisomers of Dihydrokawain and Dihydrokawain-5-ol The activity of Dihydrokawain and Dihydrokawain-5-ol were introduced and previous synthetic reports of them were introduced in brief. The enantioselective synthesis of all stereoisomers of Dihydrokawain and Dihydrokawain-5-ol was shortly achieved fromre adily available allenylboronic esters, in which condensations of aldehydes with chiral allenylboronic esters as the key step.

Chapter 5. A facile approach to synthesis of the di-O-methyl ethers of (−)-agatharesinol,(−)-sugiresinol, (+)-nyasol and (+)tetrahydronyasol The activity of (−)-agatharesinol, (−)-sugiresinol were introduced and previous synthetic reports of them were introduced in brief. The facile enantioselective synthesis of the di-O-methyl ethers of (−)agatharesinol, (−)-sugiresionl, (+)-nyasol and (+)-tetrahydronyasol were achieved in high yield. The absolute configuration of (+)-nyasol  was  confirmed  via  first  total  synthesis  of  (+)-nyasol  and 

(+)-tetrahydronyasol.

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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/262010/238707
Collection化学化工学院
Recommended Citation:
GB/T 7714
权伟国. (–)-Heliconol A、Kawain 类、二氢异香豆素类及脱碳木脂素类化合物的全合成研究[D]. 兰州. 兰州大学,2007.
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