The study of using intramolecular nucleophile substitution to synthesis the furan ring,and the synthesis of(-)-Pachastrissamine
碩士 === 國立中央大學 === 化學研究所 === 100 === (-)-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. Li...
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| Format: | Others |
| Language: | zh-TW |
| Published: |
2012
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| Online Access: | http://ndltd.ncl.edu.tw/handle/03971992450565539484 |
| Summary: | 碩士 === 國立中央大學 === 化學研究所 === 100 === (-)-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.
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