1385018-40-5Relevant academic research and scientific papers
Biomimetic total synthesis of cruentaren A via aromatization of diketodioxinones
Fouche, Marianne,Rooney, Lisa,Barrett, Anthony G. M.
, p. 3060 - 3070 (2012/05/20)
The total synthesis of cruentaren A, a biologically active resorcylate natural product, is reported. The aromatic unit was constructed via late-stage cyclization and aromatization from a diketodioxinone intermediate and macrocyclization using Fuerstner ring-closing alkyne metathesis.
Synthesis of cruentaren A
Kusuma, Bhaskar Reddy,Brandt, Gary E. L.,Blagg, Brian S. J.
, p. 6242 - 6245 (2013/02/23)
Cruentaren A, an antifungal benzolactone produced by the myxobacterium Byssovorax cruenta, is highly cytotoxic against various human cancer cell lines and a highly selective inhibitor of mitochondrial F-ATPase. A convergent and efficient synthesis of cruentaren A is reported, based upon a diastereoselective alkylation, a series of stereoselective aldol reactions utilizing Myers' pseudoephedrine propionamide, an acyl bromide mediated esterification, and a ring-closing metathesis (RCM) as the key steps. The RCM reaction was applied for the first time toward the total synthesis of cruentaren A, which led to a convergent and efficient synthesis of the natural product.
