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Construction of the Azacyclic Core of Tabernaemontanine-Related Alkaloids via Tandem Reformatsky Aza-Claisen Rearrangement
- Authors
- Suh, Young-Ger; Lim, Changjin; Sim, Jaehoon; Lee, Jae Kyun; Surh, Young-Joon; Paek, Seung-Mann
- Issue Date
- 3-Feb-2017
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.82, no.3, pp 1464 - 1470
- Pages
- 7
- Indexed
- SCI
SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 82
- Number
- 3
- Start Page
- 1464
- End Page
- 1470
- ISSN
- 0022-3263
1520-6904
- Abstract
- A divergent synthetic methodology for a tabernaemontanine-related alkaloid was developed. The synthetic route features practical improvements in the Pictet-Spengler cyclization for the tetrahydro-fi-carboline intermediate and an unprecedented tandem Reformatsky aza-Claisen rearrangement to create the core carbon skeleton and stereochemistries of tabernaemontanine-related alkaloids.
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