期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 361, 期 21, 页码 4888-4892出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900801
关键词
Cyanide; Imino-Stetter reaction; Biomimetic total synthesis; goniomitine; Asymmetric synthesis
资金
- National Research Foundation of Korea (NRF) - Korean Government [NRF-2018R1D1 A1 A02086110, NRF-2014-011165]
Concise total syntheses of rac- and (+)-goniomitine were developed. The cyanide-catalyzed imino-Stetter reaction of an aldimine, derived from ethyl 2-aminocinnamate and either rac- or (S)-alpha,beta-unsaturated aldehyde bearing a delta-valerolactam at the beta-position, provided rac- or (S)-indole-3-acetate carrying an alpha-vinyl-delta-valerolactam scaffold at the 2-position, respectively. Subsequent saturation of the vinyl group, followed by treatment with DIBAL-H, afforded N-benzyl protected goniomitine. Final debenzylation provided the desired natural product after only three column separations.
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