Asymmetric syntheses of (-)-mitorubrin and related azaphilone natural products are reported. Key steps involve copper-mediated, enantioselective oxidative dearomatization to prepare the azaphilone core and olefin cross-metathesis for side-chain installation. [reaction: see text]
[Show abstract][Hide abstract] ABSTRACT: A series of cyclohexadienones were synthesized by dearomatization of phenols followed by Dess-Martin oxidation. Asymmetric intramolecular Stetter reactions of these substrates provide hydrobenzofuranones in good to excellent yields and excellent stereoselectivities. Up to three stereocenters as well as quaternary stereocenter are formed from polysubstituted substrates. A scale up experiment demonstrates the utility of this transformation.
Organic Process Research & Development 02/2007; 11(3):598-604. DOI:10.1021/op600278f · 2.53 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
[Show abstract][Hide abstract] ABSTRACT: Converging on the target: The highly cytotoxic F-ATPase inhibitor cruentaren A constitutes an interesting lead in the quest for innovative chemotherapeutic agents for the treatment of various diseases, including cancer. Its synthesis was achieved in an overall yield of 3% by an expeditious convergent route involving a ring-closing aikyne metathesis reaction (RCAM) for the formation of the macrocyclic ring (see picture). (Chemical Equation Presented)
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