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Step-Economical Synthesis of the Marine Ascidian Antibiotics Cadiolide A, B, and D

Author:
Boukouvalas, John, Thibault, Charles
Source:
Journal of organic chemistry 2015 v.80 no.1 pp. 681-684
ISSN:
1520-6904
Subject:
antibiotics, chemical structure, condensation reactions, cycloaddition reactions, hydrolysis, organic chemistry, organic compounds
Abstract:
A concise, modular and efficient synthesis of the title natural products is reported. Prominent steps include (i) one-pot assembly of a key β-aryl-α-benzoylbutenolide building block by regiocontrolled “click–unclick” oxazole–ynone Diels–Alder cycloaddition/cycloreversion and ensuing 2-alkoxyfuran hydrolysis and (ii) a protecting group-free vinylogous Knoevenagel condensation enabling rapid access to cadiolides A, B, and D from a common precursor.
Agid:
5503558