兰州大学机构库 >化学化工学院
(–)-Bitungolide F及(–)-Pandangolide 1a的不对称合成研究
其他题名Studies on the Asymmetric Syntheses of(–)-Bitungolide F and (–)-Pandangolide 1a
苏瀛鹏
导师厍学功
学位类别博士
2009-05-27
关键词二氢吡喃酮 Bitungolide F 不对称合成 Evans-Aldol反应 类Claisen缩合反应 Julia-Kocienshi成烯反应 大环内酯 Pandangolide 1a RCM反应 Keck酯化
中文摘要本论文主要对二氢吡喃酮类天然产物Bitungolide F及大环内酯类天然产物Pandangolide 1a进行了不对称合成研究。主要包括三个部分: 一、醇氧化成醛酮方法及试剂 (综述) 从(1) 铬试剂;(2) 活化的DMSO;(3) 高价碘化合物;(4) 钌试剂;(5) TEMPO;(6) 氢转移氧化;(7) Fétizon试剂;(8) 选择性氧化等八各方面对醇氧化成醛、酮进行了综述。 二、(–)-Bitungolide F 的不对称合成研究 简要介绍了我们组对含有5, 6-二氢-α-吡喃酮环结构类化合物的合成情况。 用廉价易得的天然苹果酸为起始原料,以β-羟基诱导的还原反应、Myers甲基化反应、Evans aldol反应、类Claisen缩合反应、Julia-Kocienski偶联反应为关键步骤,以17步,20.1%的产率,完成了对(–)-bitungolide F的全合成。进一步确证天然(+)-bitungolide F的绝对构型。这一合成工作也为合成bitungolides A-E奠定了基础。 三、(–)-Pandangolide 1a的不对称合成研究 简要介绍了我们组对大环内酯类天然产物的合成情况。 以廉价易得的天然苹果酸、6-溴-1-己烯及(S)-环氧丙烷为起始原料,以Keck反应、RCM反应为关键步骤,合成了pandangolide 1a的12元环母核结构。
英文摘要This dissertation aims at the studies on the asymmetric syntheses of dihydropyrone natural product (–)-Bitungolide F and macrolide natural product (–)-pandangolide 1a. It consisted of the following three parts: Chapter 1. Methods for oxidation of alcohols to aldehydes and ketones (Review). The introduction of oxidation of alcohols to aldehydes and ketones was described, which consisted of the following eight aspects: (1) Chromium-Based Reagents; (2) Activated Dimethy Sulfoxide; (3) Hyervalent Iodine Compounds; (4) Ruthenium-Based Oxidations; (5) TEPO; (6) Oxidation by Hydride Transfer from a Metallic Alkoxide; (7) Fétizon reagent; (8) Selective Oxidations. Chapter 2. Studies on the asymmetric synthesis of (–)-Bitungolide F. The work of our group in synthesis of dihydropyrone natural products was introduced briefly. An efficient total synthesis of (–)-bitungolide F from natural malic acid in 17 steps and 20.1% yield was described. Key steps involve hydroxy-directed reduction, a Myers asymmetric alkylation, an Evans aldol reaction, a Claisen-like cyclization and a Julia-Kocienski olefination, which further confirms the absolute stereochemistry of bitungolide F and lays down a foundation for further diversity of total synthesis of bitungolides A-E. Chapter 3. Studies on the asymmetric synthesis of (–)-Pandangolide 1a. The work of our group in synthesis of macrolide natural products was introduced briefly. The efficient asymetric synthesis of 12-membered precursor of pandangolide 1a has been achieved via a Keck reaction, a RCM reaction staring from natural malic acid, (S)-proplene oxid and 6-Br-1-hexene.
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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/262010/238709
Collection化学化工学院
Recommended Citation:
GB/T 7714
苏瀛鹏. (–)-Bitungolide F及(–)-Pandangolide 1a的不对称合成研究[D]. 兰州. 兰州大学,2009.
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