Intramolecular Dearomative Inverse-Electron-Demand Diels Alder Strategy for the Total Synthesis of (+)-Alstonlarsine A
Samo za registrovane korisnike
2023
Članak u časopisu (Recenzirana verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
An evolution of a synthetic route leading to a successful enantioselective total synthesis of monoterpenoid indole alkaloid (+)-alstonlarsine A is represented. The unique 9-azatricyclo[4.3.1.03,8]decane core was assembled through an efficient domino sequence comprising enamine formation in situ, followed by intramolecular dearomative inverse-electron-demand Diels Alder reaction. The preparation of the tricyclic dihydrocyclohepta[b]indole key intermediate via the intramolecular Horner–Wadsworth–Emmons reaction required a development of a new general method for the introduction of the phosphonoacetate moiety into the indole C-2 position, through copper-carbenoid insertion. The modular nature of the represented synthetic approach makes it suitable for the synthesis of analogues with different substituents’ patterns.
Ključne reči:
Alcohols / Aldehydes / Chemical reactions / Indoles / Organic compoundsIzvor:
The Journal of Organic Chemistry, 2023, 88, 16, 11618-11626Izdavač:
- American Chemical Society
Finansiranje / projekti:
- New SMART Synthesis - New Synthetic Methods and their Applications for Rapid Total Syntheses of Complex Natural Products and Bioactive Molecules (RS-ScienceFundRS-Ideje-7750119)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200168 (Univerzitet u Beogradu, Hemijski fakultet) (RS-MESTD-inst-2020-200168)
Napomena:
- This is the peer-reviewed version of the article: Đurković, F., Ferjančić, Z.,& Bihelović, F.. (2023). Intramolecular Dearomative Inverse-Electron-Demand Diels Alder Strategy for the Total Synthesis of (+)-Alstonlarsine A. in The Journal of Organic Chemistry American Chemical Society., 88(16), 11618-11626. https://doi.org/10.1021/acs.joc.3c00923
Povezane informacije:
- Verzija dokumenta
https://doi.org/10.1021/acs.joc.3c00923 - Verzija dokumenta
https://cherry.chem.bg.ac.rs/handle/123456789/6497
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Đurković, Filip AU - Ferjančić, Zorana AU - Bihelović, Filip PY - 2023 UR - http://cherry.chem.bg.ac.rs/handle/123456789/6499 AB - An evolution of a synthetic route leading to a successful enantioselective total synthesis of monoterpenoid indole alkaloid (+)-alstonlarsine A is represented. The unique 9-azatricyclo[4.3.1.03,8]decane core was assembled through an efficient domino sequence comprising enamine formation in situ, followed by intramolecular dearomative inverse-electron-demand Diels Alder reaction. The preparation of the tricyclic dihydrocyclohepta[b]indole key intermediate via the intramolecular Horner–Wadsworth–Emmons reaction required a development of a new general method for the introduction of the phosphonoacetate moiety into the indole C-2 position, through copper-carbenoid insertion. The modular nature of the represented synthetic approach makes it suitable for the synthesis of analogues with different substituents’ patterns. PB - American Chemical Society T2 - The Journal of Organic Chemistry T1 - Intramolecular Dearomative Inverse-Electron-Demand Diels Alder Strategy for the Total Synthesis of (+)-Alstonlarsine A VL - 88 IS - 16 SP - 11618 EP - 11626 DO - 10.1021/acs.joc.3c00923 ER -
@article{ author = "Đurković, Filip and Ferjančić, Zorana and Bihelović, Filip", year = "2023", abstract = "An evolution of a synthetic route leading to a successful enantioselective total synthesis of monoterpenoid indole alkaloid (+)-alstonlarsine A is represented. The unique 9-azatricyclo[4.3.1.03,8]decane core was assembled through an efficient domino sequence comprising enamine formation in situ, followed by intramolecular dearomative inverse-electron-demand Diels Alder reaction. The preparation of the tricyclic dihydrocyclohepta[b]indole key intermediate via the intramolecular Horner–Wadsworth–Emmons reaction required a development of a new general method for the introduction of the phosphonoacetate moiety into the indole C-2 position, through copper-carbenoid insertion. The modular nature of the represented synthetic approach makes it suitable for the synthesis of analogues with different substituents’ patterns.", publisher = "American Chemical Society", journal = "The Journal of Organic Chemistry", title = "Intramolecular Dearomative Inverse-Electron-Demand Diels Alder Strategy for the Total Synthesis of (+)-Alstonlarsine A", volume = "88", number = "16", pages = "11618-11626", doi = "10.1021/acs.joc.3c00923" }
Đurković, F., Ferjančić, Z.,& Bihelović, F.. (2023). Intramolecular Dearomative Inverse-Electron-Demand Diels Alder Strategy for the Total Synthesis of (+)-Alstonlarsine A. in The Journal of Organic Chemistry American Chemical Society., 88(16), 11618-11626. https://doi.org/10.1021/acs.joc.3c00923
Đurković F, Ferjančić Z, Bihelović F. Intramolecular Dearomative Inverse-Electron-Demand Diels Alder Strategy for the Total Synthesis of (+)-Alstonlarsine A. in The Journal of Organic Chemistry. 2023;88(16):11618-11626. doi:10.1021/acs.joc.3c00923 .
Đurković, Filip, Ferjančić, Zorana, Bihelović, Filip, "Intramolecular Dearomative Inverse-Electron-Demand Diels Alder Strategy for the Total Synthesis of (+)-Alstonlarsine A" in The Journal of Organic Chemistry, 88, no. 16 (2023):11618-11626, https://doi.org/10.1021/acs.joc.3c00923 . .