Evans, David A.Cheng, Bichu2013-10-182013-10-182013Cheng, Bichu. 2013. Total Synthesis of (−)-Nakadomarin A. Doctoral dissertation, Harvard University.http://dissertations.umi.com/gsas.harvard:11106http://nrs.harvard.edu/urn-3:HUL.InstRepos:11181224A convergent and scalable total synthesis of polycyclic manzamine alkaloid (-)-nakadomarin A is described. Unsaturated bicyclic lactam fragment A was prepared from acrolein in 5 steps, and macrolactam fragment B was prepared from 3-furfural in 7 steps. A double Michael addition reaction (or cyclization) between A and B provided the desired fragment coupling product C in 79% yield and 9:1 dr on more than one-gram scale. Completion of the total synthesis of (-)-nakadomarin A was then achieved in a one-pot transformation from compound C.en-USChemistryThesis or Dissertation2013-10-1810.1021/ja404673s