Gregor Talajić, Edi Topić and Nikola Cindro, researchers of the Department of Chemistry, and Jerko Meštrović, a former student of the Department of Chemistry, have published a paper titled Total Synthesis of Penicyclone A Using a Double Grignard Reaction in the ACS Journal of Organic Chemistry (IF 4,354).
The paper describes the first total synthesis of penicyclone A, a naturally occurring polyketide. The compound features a rare spiro[5.5]lactone motif and four stereogenic centers. The synthesis uses D-ribose as the starting material and features a novel diastereospecific double Grignard addition to a sugar-derived lactone for the construction of a key tertiary alcohol intermediate, a tandem oxidation/cyclization sequence for the construction of the lactone functionality, and a late stage photooxygenation/oxidative rearrangement sequence for the installation of the enone. A reevaluation of antimicrobial activity was performed with the synthetic sample.
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