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master's thesis
Sinteza (+)-peniciklona A
Zagreb: University of Zagreb, Faculty of Science, 2023. urn:nbn:hr:217:598928
Duvnjak, Mirko
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Duvnjak, M. (2023). Sinteza (+)-peniciklona A (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:598928

Duvnjak, Mirko. "Sinteza (+)-peniciklona A." Master's thesis, University of Zagreb, Faculty of Science, 2023. https://urn.nsk.hr/urn:nbn:hr:217:598928

Duvnjak, Mirko. "Sinteza (+)-peniciklona A." Master's thesis, University of Zagreb, Faculty of Science, 2023. https://urn.nsk.hr/urn:nbn:hr:217:598928

Duvnjak, M. (2023). 'Sinteza (+)-peniciklona A', Master's thesis, University of Zagreb, Faculty of Science, accessed 22 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:598928

Duvnjak M. Sinteza (+)-peniciklona A [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2023 [cited 2024 November 22] Available at: https://urn.nsk.hr/urn:nbn:hr:217:598928

M. Duvnjak, "Sinteza (+)-peniciklona A", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2023. Available at: https://urn.nsk.hr/urn:nbn:hr:217:598928

Metadata
TitleSinteza (+)-peniciklona A
Title (english)Synthesis of (+)-penicyclone A
AuthorMirko Duvnjak
MentorNikola Cindro (mentor)
Committee memberNikola Cindro (predsjednik povjerenstva)
Committee memberMirta Rubčić (član povjerenstva)
Committee memberGordan Horvat (član povjerenstva)
Committee memberŽeljka Car (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2023-09-27, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
Peniciklon A je poliketid izoliran iz ekstrakta dubokomorske vrste gljive Penicillium sp. F23-2. Molekula peniciklona A u svojoj strukturi sadrži spiro[5.5]laktonski strukturni motiv koji ga uz velik broj kiralnih centara, visoko funkcionaliziranu cikloheksanonsku jezgru i potencijalnu antimikrobnu aktivnost čini izazovnom sintetskom metom. Cilj je ovoga rada bio sintetskim putem pripraviti (+)-peniciklon A počevši od D-riboze. U prvom je dijelu D-riboza prevedena u poznati derivat L-riboze u četiri koraka. U drugom dijelu poznatim sintetskim putem od deset koraka, kojim je pripravljen prirodni (−)-peniciklon A, dobiveni je derivat preveden u (+)-peniciklon A. Apsolutna konfiguracija konačnog spoja dodatno je potvrđena određivanjem kristalne strukture difrakcijom rendgenskog zračenja na jediničnom kristalu sintetskog intermedijera.
Abstract (english)
Penicyclone A is a polyketide isolated from the extract of the deep-sea-derived fungus Penicillium sp. F23-2. The molecular structure of penicyclone A contains a spiro[5,5]lactone which, along with its many stereocenters and a highly functionalized cyclohexanone core, presents a considerable synthetic challenge. The goal of this study was to synthesize (+)-penicyclone A from D-ribose as the starting material. First, D-ribose was converted to a known L-ribose derivative in four steps. In a reaction sequence of ten steps, by which the natural enantiomer (−)-penicyclone A was obtained, the known L-ribose derivative was converted to (+)-penicyclone A. The absolute configuration of the final compound was determined by single crystal X-ray diffraction on a sample of a synthetic intermediate.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:598928
ProjectNumber: IP-2019-04-9560
Title: Koordinacijske reakcije makrocikličkih liganada u otopini
Title: Coordination Reactions of Macrocyclic Ligands in Solution
Acronym: MacroSol
Leader: Vladislav Tomišić
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
Study programmeTitle: Graduate university studies in chemistry; specializations in: Research programme
Course: Research programme
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2023-10-12 15:25:26