1234572-98-5Relevant 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.
A formal total synthesis of pahnerolide A
Gowrisankar, Parthasarathy,Pujari, Sandip A.,Kaliappan, Krishna P.
supporting information; experimental part, p. 5858 - 5862 (2010/09/05)
(Figure Presented) Under the sea: An efficient formal total synthesis of the marine natural product palmerolide A is reported herein, involving 24 longest linear steps. The key features of our synthesis involve a combination of Sharpless epoxidation and Shimizu reaction to construct the syn aldol moiety, a JuliaKocienski reaction to construct the diene, and ring-closing metathesis to form the macrocycle (see scheme; PG = protecting group).
