Sinteza (+)-peniciklona A

master's thesis

• Title (english): Synthesis of (+)-penicyclone A
• Author: Mirko Duvnjak
• Mentor: Nikola Cindro (mentor)
• Committee member: Nikola Cindro (predsjednik povjerenstva)
• Committee member: Mirta Rubčić (član povjerenstva)
• Committee member: Gordan Horvat (član povjerenstva)
• Committee member: Željka Car (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2023-09-27, 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: antibiotik; Grignardova reakcija; poliketid; totalna sinteza
• Keywords (english): antibiotic; Grignard reaction; polyketide; total synthesis
• Language: croatian
• URN:NBN: urn:nbn:hr:217:598928
• Project: Number: 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 programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-10-12 15:25:26