Total Synthesis of Pikrosalvin, Simplexene C, D and Synthetic Studies toward Swartziarboreol G and Simplexene B

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/76658

Title:	Total Synthesis of Pikrosalvin, Simplexene C, D and Synthetic Studies toward Swartziarboreol G and Simplexene B
Authors:	黃柔潔;Huang, Rou-Jie
Contributors:	化學學系
Keywords:	天然物全合成;多烯環化反應;total synthesis of natural products;polyene cyclization;cassane-type diterpenes
Date:	2018-07-17
Issue Date:	2018-08-31 11:32:18 (UTC+8)
Publisher:	國立中央大學
Abstract:	本論文敘述Simplexene C, D和Pikrosalvin 之全合成，以及Swartziarboreol G和Simplexene B之合成研究。Swartziarboreol G and Simplexene B, C, D為一種新發現具有抗白色念珠菌活性的cassane類型的二萜類化合物，另一種結構非常類似的天然物Pikrosalvin為1962年從鼠尾草葉子中分離出來，尚未進行任何活性測試。合成上，我們以香草酸 (vanillic acid) 為起始物，先進行官能基的轉換、保護，經由親電芳香取代引入三甲基矽 (TMS) 基團以及ㄧ鍋化 (one-pot) 反應一步製備出二烯化合物，再利用實驗室所新開發的多烯環化方法建立反式十氫萘核心骨架，接著將三甲基矽基團置換成碘化物以進行Suzuki 耦合反應得到苯乙烯，然後經由氧化內酯化反應得到甲基內酯 (methyl lactone) 再將甲基芳基醚水解去甲基完成Pikrosalvin之全合成，另外，以同樣的苯乙烯中間體進行氧化內酯化建立羥基內酯 (hydroxy lactone)，接著將保護基移除後以高效液相層析法掌性分離管柱 (chiral HPLC column) 分離異構物，完成Simplexene C之全合成，最後再對其中一個異構物進行甲基芳基醚水解去甲基即可得到天然物Simplexene D。　　本論文合成重點為利用本實驗室所開發的多烯環化反應方法，將其應用在天然物Simplexene B, C, D、Swartziarboreol G和Pikrosalvin 之全合成研究上，以增加其應用性。 ;The new anti-Candida cassane-type diterpenes Swartziarboreol G and Simplexene B, C, D were isolated from the root bark of Panamanian plant Swartzia simplex by Queiroz et al. in 2015. These secondary metabolites exhibited a strong antifungal activity against Candida albicans. Another natural product Pikrosalvin was isolated from the leaf of Salvia officinalis in 1962 with similar structure to Swartziarboreol G and Simplexene B, C, D. The need for further biological investigations prompted us to conduct the synthetic studies. A number of polyene cyclization methods have been reported for the total synthesis of 　polycyclic natural products. We applied a new polyene cyclization method, which was developed by our group as a key step for the total synthesis of these natural products. So far, we have finished the total synthesis of Pikrosalvin, Simplexene C and Simplexene D.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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