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Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4+3] Cycloaddition/SmI2-Pinacol Coupling
- Issue Date
- Jun-2015
- Publisher
- American Chemical Society
- Keywords
- SYNAPTOLEPIS-KIRKII; 1ST SYNTHESIS; LATENT HIV; RESINIFERATOXIN; TIGLIANE; DITERPENES; CYCLOADDITIONS; CONSTRUCTION; PROSTRATIN; PHORBOL
- Citation
- Organic Letters, v.17, no.11, pp 2672 - 2675
- Pages
- 4
- Indexed
- SCI
SCIE
SCOPUS
- Journal Title
- Organic Letters
- Volume
- 17
- Number
- 11
- Start Page
- 2672
- End Page
- 2675
- ISSN
- 1523-7060
1523-7052
- Abstract
- A synthetic approach toward the tricyclic 5,7,6-membered ring structure Of daphnane-family natural products is described. An intramolecular [4 + 3] cycloaddition reaction of furan with an oxypentadienyl cation constructed the oxa-bridged bicyclic structure in a stereoselective fashion. Structural analysis revealed that the desired exo isomer was predominantly acquired through epimerization. Finally, formation of the five-membered ring was achieved through SmI2-mediated pinacol coupling.
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Related Researcher
- Min, Sun Joon
- ERICA 공학대학 (ERICA 에너지바이오학과)