α-Diazoketones undergo smooth coupling with aryl 1,2-diamines in the presence of 10 mol % of copper(II) triflate to provide the corresponding 2-alkyl- or 2-aryl-quinoxalines in excellent yields with high selectivity. Rh2(OAc)4 is also found to be an equally effective catalyst for this transformation. It is a new and alternative approach for the preparation of biologically well-defined quinoxaline derivatives.
An efficient total synthesis of the ten-membered macrolide, xestodecalactone C is described. The synthetic sequence uses Barbier-allylation, LiAlH 4 /LiI-mediated syn-stereoselective 1,3-asymmetric reduction, and intramolecular Friedel-Crafts acylation as key steps.
An efficient total synthesis of the cytotoxic spiroketal natural products aculeatin A and B is described. The synthesis of the 1,3,5-triol moiety with appropriate configuration was accomplished from the commercially available l-malic acid. The key steps in this synthesis are the Barbier allylation, LiAlH 4 /LiI-mediated syn-stereoselective 1,3-asymmetric reduction, and phenyliodine bis(trifluoroacetate) (¼ [bis(trifluoroacetoxy)iodo]benzene; PIFA) mediated oxidative spirocyclization.
The stereoselective total synthesis of an antiproliferative and antifungal a-pyrone natural product (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one is described. The key steps involved are the Prins cyclization, Mitsunobu reaction, and ring-closing metathesis reaction.
Alcohols Q 0230Magnesium-Cadmium Chloride, a Bimetallic Catalyst System for the Allylation of Aldehydes with Allyl Bromide: An Efficient Protocol for the Synthesis of Homoallylic Alcohols -[as important building blocks of biologically active compounds]. -(NARSAIAH*, A. V.; REDDY, A. R.; RAO, Y. G.; KUMAR, E. V.; PRAKASHAM, R. S.; REDDY, B. V. S.; YADAV, J. S.; Synthesis 2008, 21, 3461-3464; Org. Chem. Div., Indian Inst. Chem. Technol., Hyderabad 500 007, India; Eng.) -Mais 11-080
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