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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

Authors
Tam, Nguyen ThanhChang, JayhyokJung, Eun-JuCho, Cheon-Gyu
Issue Date
Aug-2008
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.73, no.16, pp.6258 - 6264
Indexed
SCIE
SCOPUS
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
Volume
73
Number
16
Start Page
6258
End Page
6264
URI
https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/178109
DOI
10.1021/jo8008353
ISSN
0022-3263
Abstract
[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.
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