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Short Paper | Regular issue | Vol 92, No. 7, 2016, pp.1313-1327
Published online, 25th May, 2016
DOI: 10.3987/COM-16-13489
Approach to Phenanthroindolizidine Alkaloids Using Organic Azides with 1-Aryl Allylic Alcohols: Unexpected Tandem Reactions to Indenyl Aziridines via Nazarov Cyclization

Taiki Yokoi, Takahiro Sugiura, Hiroki Tanimoto,* Tsumoru Morimoto, Yasuhiro Nishiyama, and Kiyomi Kakiuchi

*Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan


Organic azide cyclization reactions with 1-aryl allylic alcohols were investigated in a synthetic study of phenanthroindolizidine alkaloids. Unsaturated imines (enimines) were effectively obtained from the allylic alcohol adjacent to electron-rich aromatic rings under thermal reaction conditions. The tandem aziridination-Nazarov reactions to indenyl aziridines were preferred to the acid-mediated enimine formation via Schmidt reaction in the case of 3-aryl diallylic alcohols.