First Total Synthesis of Varioxiranol A

Autor: Angelika Lásiková, Jana Doháňošová, Mária Štiblariková, Martin Parák, Ján Moncol, Tibor Gracza
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Molecules, Vol 24, Iss 5, p 862 (2019)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules24050862
Popis: The paper describes the first total synthesis of natural varioxiranol A by chiral pool approach and confirmation of its absolute configuration by single-crystal X-ray analysis. The target varioxiranol A and its 4-epimer were obtained after 10 steps from single and available chiral source 1,2-O-isopropylidene-d-glyceraldehyde in an overall yield of 10% and 6%, respectively. A synthetic strategy based on the Julia–Kocieński coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols).
Databáze: Directory of Open Access Journals
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