5091-02-1Relevant academic research and scientific papers
Bi(OTf)3-catalyzed acylation of p-quinones: A facile synthesis of acylated hydroquinones
Yadav,Reddy, B. V. Subba,Swamy,Rao, K. Raghavender
, p. 6037 - 6039 (2007/10/03)
p-Quinones undergo smooth acylation with acetic anhydride in the presence of 2mol% of bismuth triflate under mild conditions to afford the corresponding 1,4-diacylated-2-acetoxylated hydroquinones in excellent yields with high selectivity.
Diels-Alder Approaches to Model Compounds Related to Fredericamycin A
Evans, Jonathan C.,Klix, Russell C.,Bach, Robert D.
, p. 5519 - 5527 (2007/10/02)
A series of model compounds related to the antitumor and antibiotic compound fredericamycin A has been prepared.Spiro-2,5-dione (2) has been prepared and established as a novel spiro dienophile in the Diels-Alder reaction with 1,3-butadiene, Danishefsky's diene, a triacetoxy-substituted o-quinodimethane, and two isobenzofuran intermediates.Thus, the cycloaddition of 3-cyano-4,5,7-trimethoxy-1(3H)-isobenzofuranone (35) and 2 afforded 4,9-dihydroxy-5,6,8-trimethoxyspiroindene-2,1'-indan>-1,3-dione (38) in 62percent yield.This methodology provides a viable synthetic route to the quinone portion of fredericamycin A that contains the seven requisite oxygens.
