Pregled bibliografske jedinice broj: 1228425
Total synthesis of Penicyclone A using a double Grignard reaction
Total synthesis of Penicyclone A using a double Grignard reaction // Journal of organic chemistry, 87 (2022), 23; 16054-16062 doi:10.1021/acs.joc.2c02200 (međunarodna recenzija, članak, znanstveni)
CROSBI ID: 1228425 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
Total synthesis of Penicyclone A using a double
Grignard reaction
Autori
Talajić, Gregor ; Topić, Edi ; Meštrović, Jerko ; Cindro, Nikola
Izvornik
Journal of organic chemistry (0022-3263) 87
(2022), 23;
16054-16062
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
Total synthesis ; Penicyclone A ; Grignard reaction
Sažetak
We describe the first total synthesis of penicyclone A, a novel deep-sea fungus-derived polyketide, and a reevaluation of its antimicrobial activity. The synthesis of this unique spirolactone was achieved in ten steps starting from a known D-ribose derivative. The key steps include a double Grignard reaction for the diastereoselective construction of the chiral tertiary alcohol intermediate, tandem oxidation/cyclization, and a photooxygenation, followed by an oxidative rearrangement to introduce the enone functionality.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
POVEZANOST RADA
Projekti:
HRZZ-IP-2019-04-9560 - Koordinacijske reakcije makrocikličkih liganada u otopini (MacroSol) (Tomišić, Vladislav, HRZZ - 2019-04) ( CroRIS)
Ustanove:
Prirodoslovno-matematički fakultet, Zagreb
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
- Scopus
- MEDLINE
