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)-α,β-unsaturated aldehyde bearing a δ-valerolactam at the β-position, provided rac- or (S)-indole-3-acetate carrying an α-vinyl-δ-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. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 4888-4892 |
| Number of pages | 5 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 361 |
| Issue number | 21 |
| DOIs | |
| Publication status | Published - 2019 Nov 5 |
Bibliographical note
Funding Information:This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF‐2018R1D1 A1 A02086110 and NRF‐2014‐011165, Center for New Directions in Organic Synthesis).
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- Asymmetric synthesis
- Biomimetic total synthesis
- Cyanide
- Imino-Stetter reaction
- goniomitine
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry