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Total Syntheses of rac- and (+)-Goniomitine
- Authors
- Park, Eunjoon; Cheon, Cheol-Hong
- Issue Date
- 5-11월-2019
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Cyanide; Imino-Stetter reaction; Biomimetic total synthesis; goniomitine; Asymmetric synthesis
- Citation
- ADVANCED SYNTHESIS & CATALYSIS, v.361, no.21, pp.4888 - 4892
- Indexed
- SCIE
SCOPUS
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Volume
- 361
- Number
- 21
- Start Page
- 4888
- End Page
- 4892
- ISSN
- 1615-4150
- Abstract
- 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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