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Total syntheses of (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a-epi-crinamine via the regioselective synthesis and Diels-Alder reaction of 3-aryl-5-bromo-2-pyrone
- Tam, Nguyen Thanh;
- Chang, Jayhyok;
- Jung, Eun-Ju;
- Cho, Cheon-Gyu
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52초록
[GRAPHICS] We have devised a new unified synthetic protocol to (+/-)-crinine, (+/-)-crinamine, and (+/-)-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 prepared from the C3-selective Stille coupling reaction of 3,5-dibromo-2-pyrone. Also noted is that the vinyl bromide can be used as a handle for further derivatization.
키워드
AZA-COPE REARRANGEMENTS; AMARYLLIDACEAE ALKALOIDS; CYCLOADDITIONS; TANDEM; CIS-3A-ARYLOCTAHYDROINDOLES; 3,5-DIBROMO-2-PYRONE; (-)-HAEMANTHIDINE; (-)-AMABILINE; CRININE; ROUTE
- 제목
- Total syntheses of (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a-epi-crinamine via the regioselective synthesis and Diels-Alder reaction of 3-aryl-5-bromo-2-pyrone
- 저자
- Tam, Nguyen Thanh; Chang, Jayhyok; Jung, Eun-Ju; Cho, Cheon-Gyu
- 발행일
- 2008-08
- 유형
- Article
- 권
- 73
- 호
- 16
- 페이지
- 6258 ~ 6264