Pseudoguaianolides from Intramolecular Cycloadditions of Aryl Diazoketones: Synthesis of (+/-)-Confertin and an Approach to the Synthesis of (+/-)-Damsin
Rhodium(II) mandelate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acids produces bicyclodecatrienones, 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.
Kennedy, Michael,McKervey, M. Anthony
p. 2565 - 2574
(2007/10/02)
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