Total Synthesis of (+/-)-Clivonine via Diels-Alder Reactions of 3,5-Dibromo-2-pyrone
- Authors
- Wang, Cheng-dong; Chen, Qinyang; Shin, Seunghoon; Cho, Cheon-Gyu
- Issue Date
- Aug-2020
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.85, no.15, pp.10035 - 10049
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 85
- Number
- 15
- Start Page
- 10035
- End Page
- 10049
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/145320
- DOI
- 10.1021/acs.joc.0c01283
- ISSN
- 0022-3263
- Abstract
- New synthetic routes to (+/-)-clivonine were devised starting with the Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone with styrene pinacol boronate dienophiles. In the first-generation synthesis, the pivotal perhydroindoline system including the CS-hydroxyl group was constructed via a reaction sequence involving the Eschenmoser-Claisen rearrangement and regio/stereoselective epoxide opening reaction. In the second-generation synthesis, a radical-mediated cyclization approach was employed for the rapid assembly of the pyrrolidine ring. In this route, the C5-hydroxyl group provided by the dienophile in a stereochemically defined form was preserved throughout the synthesis.
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