分子內親核取代反應合成呋喃環之探討 ─ (-)-Pachastrissamine之合成

The study of using intramolecular nucleophile substitution to synthesis the furan ring,and the synthesis of(-)-Pachastrissamine

林振暐(Cheng-Wei Lin)

指導教授 ： 侯敦仁

國立中央大學/理學院/化學系/碩士(2012年)

摘要

利用掌性的雙烯雙醇((3R,4R)-hexa-1,5-diene-3,4,-diol)48為起始物合成(-)-Pachastrissamine。在此我們利用雙烯雙醇48進行Sharpless環氧化反應，建構出第三個掌性中心。之後將兩個醇基做上保護，並利用碘化鋰(lithium iodide)進行開環反應。再利用疊氮化鈉(sodium azide)以及三苯膦(triphenyl phosphine)得到氮丙啶(aziridine)，將新建構出來的第三個掌性中心進行反轉，之後以氫氟酸進行分子內親核取代(intramolecular nucleophilic substitution)合成呋喃環。最後利用交叉置換(cross metathesis)反應、氫化反應(hydrogenation)，合成出(-)-Pachastrissamine。

關鍵字

呋喃環 ； 氫氟酸

並列摘要

(-)-Pachastrissamine was synthesized using (3R,4R)-hexa-
1,5-diene-3,4-diol 48 as the starting material. We applied Sharpless epoxidation to create the third chirality center. Tert-Butyldimethylsilyl chloride was used to protect the remaing two hydroxyl groups. Lithium iodie was used to open the epoxides. Next, triphenylphosphine and sodium azide was used to yield aziridine, so the chirality center on the
epoxides was inverted. Hydrofluoric acid was applied to promote the intramolecular nucleophilic substitution to give the tetrahydrohuran. The synthesis of (-)-Pachastrissamine was achieved by cross metathesis and hydrogenation.

並列關鍵字

(-)-Pachastrissamine ； nucleophile substitution

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