1155337-76-0Relevant academic research and scientific papers
A convergent route for the total synthesis of malyngamides O, P, Q, and R
Chen, Jie,Fu, Xiao-Gang,Zhou, Ling,Zhang, Jun-Tao,Qi, Xian-Liang,Cao, Xiao-Ping
supporting information; experimental part, p. 4149 - 4157 (2009/09/08)
(Chemical Equation Presented) A convergent, enantioselective and general synthetic route to a class of marine natural products - malyngamides O (1), P (2), Q (3), R (4), 5″-epi-3 and 5″-epi-4 - bearing a novel vinyl chloride structural motif was developed. The key steps involved construction of the vinyl chloride functionality by Wittig reaction, a DCC/HOBt-promoted amidation, an aldol reaction in the construction of the basic backbone of 1, 2, 3, 4, 5″-epi-3, and 5″-epi-4, and methylation of an enol moiety via either base/acid conditions or a Mitsunobu reaction. Moreover, the absolute configuration of the stereogenic center at C-5″ in 3 was further confirmed by synthesis of the natural product and its C-5″ epimer.
