Total Synthesis of (±)-Clivonine via Diels–Alder Reactions of 3,5-Dibromo-2-pyrone
- Title
- Total Synthesis of (±)-Clivonine via Diels–Alder Reactions of 3,5-Dibromo-2-pyrone
- Author
- 신승훈
- Keywords
- ALKALOIDS CLIVONINE; AMARYLLIDACEAE; MILD; STEREOCHEMISTRY; NOBILISITINE; CYCLIZATION; FIXATION; LYCORINE; ALCOHOLS; CASCADE
- Issue Date
- 2020-07
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v. 85, no. 15, page. 10035-10049
- 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 C5-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.
- URI
- https://pubs.acs.org/doi/10.1021/acs.joc.0c01283https://repository.hanyang.ac.kr/handle/20.500.11754/169537
- ISSN
- 0022-3263; 1520-6904
- DOI
- 10.1021/acs.joc.0c01283
- Appears in Collections:
- COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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