934296-35-2Relevant academic research and scientific papers
Aza-[3 + 3] annulations. Part 6. Total syntheses of putative (-)-lepadiformine and (-)-cylindricine C
Wang, Jiashi,Swidorski, Jacob J.,Sydorenko, Nadiya,Hsung, Richard P.,Coverdale, Heather A.,Kuyava, Jennifer M.,Liu, Jia
, p. 423 - 459 (2007/10/03)
Efforts in achieving an enantioselective total synthesis of (-)-cylindricine C along with the syntheses of putative lepadiformine, epi-lepadiformines, (-)-4-deoxo-cylindricine C, and (-?-2-epi-cylindricine C are described here in details. These syntheses feature a stereoselective intramolecular aza-[3 + 3] annulation as a unified strategy, and specifically, the total synthesis of (-)-cylindricine C was accomplished in 22 steps with a 4.5% overall yield from L-serine. In addition, we developed an interesting halohydrin formation for the construction of the C4-ketone of cylindricines.
