Regioselective Synthesis and Diels-Alder Reaction of 3-substituted-5-Bromo-2-pyrones for Total Syntheses of joubertinamine, crinine, crinamine, 6a-epi-crinamine, and aspidospermidine
- Title
- Regioselective Synthesis and Diels-Alder Reaction of 3-substituted-5-Bromo-2-pyrones for Total Syntheses of joubertinamine, crinine, crinamine, 6a-epi-crinamine, and aspidospermidine
- Author
- 구엔탕탐
- Alternative Author(s)
- Nguyen Thanh Tam
- Advisor(s)
- 조천규
- Issue Date
- 2009-02
- Publisher
- 한양대학교
- Degree
- Doctor
- Abstract
- The total synthesis of (±)-joubertinamine has been achieved from 3,5-dibromo-2-pyrone in 9.6% total yield over 10 steps via the regioselective synthesis and Diels-Alder cycloaddition reaction of 3-(3,4-dimethoxyphenyl)-5-bromo-2-pyrone with phenyl vinyl sulfide.
We also devised a new unified synthetic protocol to (±)-crinine, (±)-crinamine, (±)-6a-epi-crinamine from the Diels-Alder cycloadduct of 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone with TBS vinyl ether. The requisite 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone was also prepared from the C3-selective Stille coupling reaction of 3,5-dibromo-2-pyrone. The vinyl bromide group can be used as a handle for further derivatization.
We have completed total synthesis of (±)-aspidospermidine using the 2-pyrone regioselective coupling / Diels- Alder reaction strategy. The requisite 3-ethyl-5-bromo-2-pyrone was prepared via the C3-selective Suzuki coupling reaction of 3,5-dibromo-2-pyrone.
- URI
- https://repository.hanyang.ac.kr/handle/20.500.11754/144516http://hanyang.dcollection.net/common/orgView/200000410707
- Appears in Collections:
- GRADUATE SCHOOL[S](대학원) > CHEMISTRY(화학과) > Theses (Ph.D.)
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