Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

• Aaron H. Shoemaker,
• Elizabeth A. Foker,
• Elena P. Uttaro,
• Sarah K. Beitel and
• Daniel R. Griffith

Beilstein J. Org. Chem. 2023, 19, 1615–1619, doi:10.3762/bjoc.19.118

• related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield. Keywords: alkaloids; azabicycles; Heck reaction; iron complex; tropone; Introduction Azapolycycles are embedded within numerous biologically active alkaloids [1] and pharmaceuticals [2]. As such, novel approaches to the synthesis of

• the isomeric enecarbamate 19 (the precise product ratio was variable across several trials, since the ratio of the two compounds was observed to change upon subjection of the crude product mixture to column chromatography). Conclusion In conclusion, we have shown that bridged azabicycles common to a

Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

• Dimas J. P. Lima,
• Antonio E. G. Santana,
• Michael A. Birkett and
• Ricardo S. Porto

Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

• the enatiopure azabicycles. This 6-step sequence was successfully completed and (−)-adaline (1) and (−)-euphococcinine (2) were prepared in overall yields of 11.9% and 15.2%, respectively. Specific rotation measured for (−)-adaline (1) was [α]D20 −12.2 (c 1.1, CHCl3); {lit. [α]D20 −11 (c 2, CHCl3