68252-11-9Relevant academic research and scientific papers
An Approach to Cytochalasan Synthesis: Macrolide Formation by an Intramolecular Diels-Alder Reaction. X-Ray Structure of Methyl (1RS, 2SR, 5RS, 6RS)-2,5-Dimethyl-1-hydroxy-6-cyclohex-3-ene-1-carboxylate
Bailey, Stephen J.,Thomas, Eric J.,Vather, Sunil M.,Wallis, John
, p. 851 - 860 (2007/10/02)
When heated in toluene under reflux, under high dilution conditions, trans,trans-hexadeca-12,14-dienoyl-oxymaleic anhydride (4) cyclised via an intramolecular Diels-Alder reaction to give the macrocyclic lactone (5) in 27percent yield together with 5percent of a regioisomer (23). (1RS, 2SR, 5RS, 6RS)-2,5-Dimethyl-1-octanoyloxycyclohex-3-ene-1,6-dicarboxylic acid anhydride (11) was converted into the methyl (1RS, 2SR, 5RS, 6RS)-2,5-dimethyl-1-octanoyloxy-6-benzylcarbonylcyclohex-3-ene-1-carboxylate (33), but selective reduction of this ketone was unsuccessful.The structure of one of the reduction products, methyl (1RS, 2SR, 5RS, 6RS)-2,5-dimethyl-1-hydroxy-6-cyclohex-3-ene-1-carboxylate (35) was confirmed by an X-ray structure determination.
