831228-09-2Relevant academic research and scientific papers
A shimizu non-aldol approach to the formal total synthesis of palmerolide A
Pujari, Sandip A.,Gowrisankar, Parthasarathy,Kaliappan, Krishna P.
, p. 3137 - 3151 (2012/08/28)
A formal total synthesis of palmerolide A has been accomplished by assembling three fragments by means of successive Julia-Kocienski olefination, Yamaguchi esterification, and ring-closing metathesis (RCM). Our initial efforts to combine the first two fragments through a Julia-Kocienski reaction between a secondary sulfone and a ketone were not successful; nevertheless, it was feasible between a primary sulfone and aldehyde. Yamaguchi esterification with the third fragment then set the stage for a RCM reaction. Initial failure of the RCM with a PMB-ether adjacent to the olefins and the difficulty in cleaving the PMB-ether prompted us to change the choice of protecting groups, which then paved the way to the macrocyclic core of palmerolide A.
