人參中長鏈不飽和環氧化合物之合成研究

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Title:	人參中長鏈不飽和環氧化合物之合成研究 Synthetic Study of a long-chain epoxide in Panax ginseng
Authors:	雷濟帆
Contributors:	應用化學研究所
Keywords:	人參 Panax ginseng
Date:	2007
Issue Date:	2010-07-05 09:27:40 (UTC+8)
Abstract:	近年來從人參中分離出polyacetylene類化合物，其基本上多為包含十七個碳的1,3-diynol，其中一些成分具有抗腫瘤活性。雖然有許多人參成分的研究報告，但是合成的報告卻不多。本篇是以合成人參中長鏈不飽和環氧化合物ginsenoyne A為目的，以便探討人參中具有抗腫瘤活性的ginsenoyne A及其立體異構物的結構與活性之關聯性。從逆合成途徑來看，ginsenoyne A可以利用(R)-5-bromopent-1-en- 4-yn-3-ol和(2S,3R)-2-(hept-6-enyl)-3-(prop-2-ynyl)oxirane進行Cadiot-Chodkiewicz cross-coupling來合成。本論文主要研究在於(2S,3R)-2-(hept-6-enyl)-3-(prop-2-ynyl)oxirane，它是以methyl oleate或2-octyn-1-ol為起始物來進行合成，其中2S,3R的立體結構是藉由不對稱dihydroxylation反應所建立的。 Panax ginseng C. A. Meyer is one of the most important oriental medicinal plant in Japan, Korea and China. Many unusual polyacetylene compounds were isolated from Panax ginseng and showed to suppress the in vitro growth of cultured tumor cells. In this thesis, we investigated the synthesis of a long-chain epoxide, ginsenoyne A, in order to study the relationship of structure and activity of ginsenoyne A. Retrosynthetically, the synthetic building blocks of ginsenoyne A can be (R)-5-bromopent-1-en-4-yn-3-ol and (2S,3R)-2-(hept-6-enyl)-3- (prop-2-ynyl)oxirane. These compounds can be linked using a key Cadiot-Chodkiewicz cross-coupling reaction. The thesis concentrates on the synthesis of (2S,3R)-2-(hept-6-enyl)-3-(prop-2-ynyl)oxirane, starting from methyl oleate or 2-octyn-1-ol. Its 2S,3R configuration was obtained by Sharpless asymmetric dihydroxylation.
Appears in Collections:	[Department of Chemistry & Graduate Institute of Applied Chemistry ] thesis

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