Pseudoguaianolides from Intramolecular Cycloadditions of Aryl Diazoketones: Synthesis of (+/-)-Confertin and an Approach to the Synthesis of (+/-)-Damsin

Article abstract of DOI:10.1039/P19910002565

Rhodium(II) mandelate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acids produces bicyclo<5.3.0>decatrienones, one of which has been used to synthesise an advanced (+/-)-confertin intermediate in six stages and 20percent overall yield.The possibility of constructing intermediates for the synthesis of damsin-like pseudoguaianolides via catalysed diazoketone cyclisation is also examined and methods for the construction of polyfunctional 3-arylpropionic acids suitable for use as damsin precursors are presented.