Total Syntheses of rac- and (+)-Goniomitine

Eunjoon Park, Cheol Hong Cheon

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)4888-4892
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume361
Issue number21
DOIs
Publication statusPublished - 2019 Nov 5

Keywords

  • Asymmetric synthesis
  • Biomimetic total synthesis
  • Cyanide
  • goniomitine
  • Imino-Stetter reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Total Syntheses of rac- and (+)-Goniomitine. / Park, Eunjoon; Cheon, Cheol Hong.

In: Advanced Synthesis and Catalysis, Vol. 361, No. 21, 05.11.2019, p. 4888-4892.

Research output: Contribution to journalArticle

Park, Eunjoon ; Cheon, Cheol Hong. / Total Syntheses of rac- and (+)-Goniomitine. In: Advanced Synthesis and Catalysis. 2019 ; Vol. 361, No. 21. pp. 4888-4892.
@article{2491d7d1de5f4dd5bd8c66046ed9f700,
title = "Total Syntheses of rac- and (+)-Goniomitine",
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.).",
keywords = "Asymmetric synthesis, Biomimetic total synthesis, Cyanide, goniomitine, Imino-Stetter reaction",
author = "Eunjoon Park and Cheon, {Cheol Hong}",
year = "2019",
month = "11",
day = "5",
doi = "10.1002/adsc.201900801",
language = "English",
volume = "361",
pages = "4888--4892",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-VCH Verlag",
number = "21",

}

TY - JOUR

T1 - Total Syntheses of rac- and (+)-Goniomitine

AU - Park, Eunjoon

AU - Cheon, Cheol Hong

PY - 2019/11/5

Y1 - 2019/11/5

N2 - 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.).

AB - 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.).

KW - Asymmetric synthesis

KW - Biomimetic total synthesis

KW - Cyanide

KW - goniomitine

KW - Imino-Stetter reaction

UR - http://www.scopus.com/inward/record.url?scp=85073808447&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85073808447&partnerID=8YFLogxK

U2 - 10.1002/adsc.201900801

DO - 10.1002/adsc.201900801

M3 - Article

AN - SCOPUS:85073808447

VL - 361

SP - 4888

EP - 4892

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 21

ER -