Synthesis of the Proposed Structures of Parvistemoamide and Their Transformations to Stemoamide Derivatives

The proposed structures of parvistemoamide have been achieved by macrolactamization, but none of the characterization data of synthetic samples matched with those of the natural sample. The transformation of the highly strained 10-membered lactam ring in parvistemoamide into the pyrrolo[1,2-alpha]-azepine nucleus in stemoamide is accomplished for the first time by either transannular cyclization or Pilli's transformation. This research may promote the total synthesis of other more complex stemoamide-type or medium-sized-ringcontaining Stemona alkaloids.

Automated summary

The proposed structures of parvistemoamide have been achieved by macrolactamization, but characterization data of synthetic samples did not match with those of the natural sample. The transformation of the highly strained 10-membered lactam ring in parvistemoamide into the pyrrolo[1,2-alpha]-azepine nucleus in stemoamide is accomplished for the first time by either transannular cyclization or Pilli's transformation. This research may promote the total synthesis of other more complex stemoamide-type or medium-sized-ringcontaining Stemona alkaloids.