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Paper | Special issue | Vol 70, No. 1, 2006, pp.423-459
Published online, 24th October, 2006
DOI: 10.3987/COM-06-S(W)40
Aza-[3+3] Annulations. Part 6. Total Synthesis of Putative (-)-Lepadiformine and (-)-Cylindricine C

Jiashi Wang, Jacob J. Swidorski, Nadiya Sydorenko, Richard P. Hsung,* Heather A. Coverdale, Jennifer M. Kuyava, and Jia Liu

*Department of Chemistry, University of Minnesota, 207 Pleasant Street S. E. Minneapolis, MN 55455-0431, U.S.A.

Abstract

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.