prikaz prve stranice dokumenta Totalna sinteza peniciklona A
Embargo period 2025-06-14
doctoral thesis
Totalna sinteza peniciklona A
Zagreb: University of Zagreb, Faculty of Science, 2024. urn:nbn:hr:217:979873
Talajić, Gregor
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Talajić, G. (2024). Totalna sinteza peniciklona A (Doctoral thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:979873

Talajić, Gregor. "Totalna sinteza peniciklona A." Doctoral thesis, University of Zagreb, Faculty of Science, 2024. https://urn.nsk.hr/urn:nbn:hr:217:979873

Talajić, Gregor. "Totalna sinteza peniciklona A." Doctoral thesis, University of Zagreb, Faculty of Science, 2024. https://urn.nsk.hr/urn:nbn:hr:217:979873

Talajić, G. (2024). 'Totalna sinteza peniciklona A', Doctoral thesis, University of Zagreb, Faculty of Science, accessed 13 July 2024, https://urn.nsk.hr/urn:nbn:hr:217:979873

Talajić G. Totalna sinteza peniciklona A [Doctoral thesis]. Zagreb: University of Zagreb, Faculty of Science; 2024 [cited 2024 July 13] Available at: https://urn.nsk.hr/urn:nbn:hr:217:979873

G. Talajić, "Totalna sinteza peniciklona A", Doctoral thesis, University of Zagreb, Faculty of Science, Zagreb, 2024. Available at: https://urn.nsk.hr/urn:nbn:hr:217:979873

Metadata
TitleTotalna sinteza peniciklona A
Title (english)Total synthesis of penicyclone A
AuthorGregor Talajić
MentorNikola Cindro (mentor)
Committee memberInes Primožič (predsjednik povjerenstva)
Committee memberDavor Margetić (član povjerenstva)
Committee memberNikola Bregović (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2024-06-14, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Universal decimal classification
(UDC)		54 - Chemistry. Crystallography. Mineralogy
Abstract
Peniciklon A je poliketid izoliran iz kulture dubokomorske gljivice Penicillium Sp. F32-2. Zanimljiva struktura ovog prirodnog spoja koji sadrži spiro[5.5]laktonsku jezgru i četiri stereogena centra te prijavljena antimikrobna aktivnost potaknule su studije o njegovoj totalnoj sintezi. U ovom radu istražena su tri fundamentalno različita pristupa sintezi peniciklona A. Prvi pristup temeljio se na razvoju oksidativne dearomatizacije fenola te daljnje funkcionalizacije dobivenog cikloheksadienona regioselektivnom cis-dihidroksilacijom. Drugi pristup temeljio se na korištenju D-(+)-kvininske kiseline kao polaznog spoja, dok se treći pristup temeljio na razvoju dijastereoselektivne dvostruke adicije Grignardovih reagensa na literaturno poznati lakton izveden iz D-riboze. Peniciklon A je uspješno pripravljen trećim pristupom. Sintetski peniciklon A pokazao je različito optičko skretanje od prirodnog materijala te nedostatak antimikrobne aktivnosti što je potaknulo sintezu i drugog enantiomera, također iz D-riboze.
Abstract (english)
Penicyclone A is a polyketide isolated from the deep-sea fungus Penicillium Sp. F32-2. Its interesting structure containing a spiro[5.5]lactone core and four stereogenic centers and the reported antimicrobial activity prompted studies in its total synthesis. Three fundamentally different approaches to the synthesis of penicyclone A were investigated. The first approach was based on the development of an oxidative dearomatization of phenols and further functionalization of the obtained cyclohexadienone by regioselective cis-dihydroxylation. The second approach was based on the use of D-(-)-quinic acid as a starting compound, while the third approach was based on the development of a diastereoselective double Grignard reaction. Penicyclone A was successfully prepared using the third approach. Synthetic penicyclone A showed differences in optical rotation and a lack of antimicrobial activity. This prompted the synthesis of the second enantiomer.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:979873
Promotion2024
Study programmeTitle: Doctoral study
Study programme type: university
Study level: postgraduate
Academic / professional title: doktor/doktorica u području prirodnih znanosti (doktor/doktorica u području prirodnih znanosti)
Type of resourceText
Extent118, CLXXVI str. ; 30 cm
File originBorn digital
Access conditionsEmbargoed access
Embargo expiration date: 2025-06-14
Terms of useLicence In copyright icon
Created on2024-06-21 11:58:26