Skip to content
DraconiticResearch
Search Sources API
197,768 studies31 sourcesUpdated 6 min ago
Peer-reviewedCC BY-NC-NDThe Journal of organic chemistry

Enantioselective Formal Synthesis of (-)-Neoxaline Enabled by an Asymmetric Ir-Catalyzed Reverse Prenylation.

  • Jonathan Farhi1
  • Brian M Stoltz1
  1. 1The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California91125, United States.
Read full textPDFDOICite

Abstract

We report the enantioselective formal synthesis of neoxaline, an archetypal member of the oxaline alkaloids. An initial approach employs an asymmetric deaminative cross-coupling to install the 1,1-dimethylallyl ("reverse prenyl") moiety onto an oxindole framework. Subsequent strategies employ iridium-catalyzed reverse prenylation onto tryptamine scaffolds, enabling the facile construction of a densely functionalized α-carboline framework. The route detailed herein represents a potentially general strategy for the synthesis of related oxaline alkaloids.

Related

  1. Convergent Approach for the Asymmetric Synthesis of Vinyl Sulfoximines via Ruthenium-Catalyzed Enantioselective Alkylation of Sulfenamides with (Diazomethyl)phosphonates
    Zachary W. Boyer, Christopher W. Smith, Jonathan A. Ellman
    Organic lettersPeer-reviewedLicence not statedFull textOrganic chemistryPMC
  2. CuBr-Catalyzed Enantioselective Synthesis of Decahydroquinoxaline-Based
    Laxman Alakonda, Mariappan Periasamy
    ChemRxivPreprintCC BYFull textOrganic chemistryChemRxiv
  3. Enantioselective Synthesis of Carbazole-Thioisatin Spirocycles via NHC-Catalyzed Remote N–H Activation
    Ladislav Lóška, Ivana Císařová, Jan Veselý
    ChemRxivPreprintCC BYFull textOrganic chemistryChemRxiv
  4. Enantioselective synthesis of axially chiral α-ketoamide diaryl ethers via asymmetric double carbonylation of cyclic iodonium salts
    Wang Yao, Xiao-Feng Wu
    Chemical sciencePeer-reviewedCC BYFull textOrganic chemistryEurope PMCEurope PMCPMC
  5. Visible Light‐Driven Copper‐Catalyzed Asymmetric Synthesis via Sequential C(sp 3 )─C(sp 3 ) Bond Scission
    Zhiyong Chi, Boxuan Yang, Xiaoling Cheng +2
    Angewandte Chemie International EditionPeer-reviewedLicence not statedFull text6 citedOrganic chemistryOpenAlex

Cite

BibTeXRIS
BibTeX
@article{farhi2026enantioselective,
  title = {{Enantioselective Formal Synthesis of (-)-Neoxaline Enabled by an Asymmetric Ir-Catalyzed Reverse Prenylation.}},
  author = {Jonathan Farhi and Brian M Stoltz},
  journal = {The Journal of organic chemistry},
  year = {2026},
  month = oct,
  doi = {10.1021/acs.joc.6c02094},
  url = {https://europepmc.org/article/MED/42917571},
  note = {CC BY-NC-ND},
}
RIS
TY  - JOUR
TI  - Enantioselective Formal Synthesis of (-)-Neoxaline Enabled by an Asymmetric Ir-Catalyzed Reverse Prenylation.
AU  - Jonathan Farhi
AU  - Brian M Stoltz
PY  - 2026
DA  - 2026/10/01
JO  - The Journal of organic chemistry
DO  - 10.1021/acs.joc.6c02094
UR  - https://europepmc.org/article/MED/42917571
AB  - We report the enantioselective formal synthesis of neoxaline, an archetypal member of the oxaline alkaloids. An initial approach employs an asymmetric deaminative cross-coupling to install the 1,1-dimethylallyl ("reverse prenyl") moiety onto an oxindole framework. Subsequent strategies employ iridium-catalyzed reverse prenylation onto tryptamine scaffolds, enabling the facile construction of a densely functionalized α-carboline framework. The route detailed herein represents a potentially general strategy for the synthesis of related oxaline alkaloids.
SN  - 0022-3263
SN  - 1520-6904
ER  -