Pregled bibliografske jedinice broj: 1265483
Total synthesis of penicyclone A
Total synthesis of penicyclone A // 28HSKIKI : 28th Croatian Meeting of Chemists and Chemical Engineers and 6th Symposium Vladimir Prelog : Book of Abstracts / Rogošić, Marko (ur.).
Zagreb: Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI), 2023. str. 12-12 (pozvano predavanje, međunarodna recenzija, sažetak, znanstveni)
CROSBI ID: 1265483 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
Total synthesis of penicyclone A
Autori
Talajić, Gregor ; Topić, Edi ; Meštrović, Jerko ; Cindro, Nikola
Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni
Izvornik
28HSKIKI : 28th Croatian Meeting of Chemists and Chemical Engineers and 6th Symposium Vladimir Prelog : Book of Abstracts
/ Rogošić, Marko - Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI), 2023, 12-12
Skup
The 28th Croatian Meeting of Chemists and Chemical Engineers (28HSKIKI) and 6th Symposium Vladimir Prelog
Mjesto i datum
Rovinj, Hrvatska, 28.03.2023. - 30.03.2023
Vrsta sudjelovanja
Pozvano predavanje
Vrsta recenzije
Međunarodna recenzija
Ključne riječi
Total synthesis ; Penicyclone A ; Grignard reaction
Sažetak
Penicylone A is a naturally occurring polyketide compound containing a spiro[5.5]lactone moiety which was recently isolated from Penicillium sp. F23-2.1 Our motivation for the synthesis of penicyclone A, aside from its exotic structure, was its reported antibacterial activity (MIC = 0.3 µg/mL for S. Aureus). The variety of functional groups and chiral centers in a relatively small molecule presented a considerable synthetic challenge. We developed the first total synthesis of penicyclone A, which was accomplished in 10 steps starting from a known D-ribose derivative.2 The key step was a double Grignard reaction enabling the diastereoselective construction of a crucial tertiary alcohol intermediate. This new methodology was also tested on several other modal compounds to determine the scope of its applicability. The synthesis also featured a tandem oxidation/cyclization for the synthesis of the lactone moiety and a photooxygenation followed by an oxidative rearrangement to introduce the enone functionality. The synthetic penicyclone A was thoroughly characterized using NMR spectroscopy, mass spectrometry, circular dichroism and optical rotation measurements. Its absolute configuration was confirmed using single crystal X-ray diffraction. After reevaluation of the reported biological activity of penicyclone A the synthetic sample showed no antimicrobial activity. Discrepancies in the values of optical rotation between the natural and synthetic sample point to the possibility that the natural compound was isolated as an enantiomeric mixture which directed the research towards the synthesis of the other enantiomer.3
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