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

• , West Common, Harpenden, AL5 2JQ, United Kingdon 10.3762/bjoc.17.4 Abstract The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (−)-Adaline (1) and (+)-euphococcinine (2), found in secretions of Coccinelid beetles, and (+)-N-methyleuphococcinine (3

• chemical ecology of Adalia bipunctata and the recent methodologies to obtain adaline (1), euphococcinine (2), and N-methyleuphococcinine (3). Keywords: 9-azabicyclo[3.3.1]nonane; Coccinelid beetles; dipolar cycloaddition; homotropane; ring-closing metathesis; Introduction Coccinellid beetles contain a

Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (±)-hippodamine and (±)-epi-hippodamine

• Annabella F. Newton,
• Martin Rejzek,
• Marie-Lyne Alcaraz and
• Robert A. Stockman

Beilstein J. Org. Chem. 2008, 4, No. 4, doi:10.1186/1860-5397-4-4

• . To further test this theory significant amounts of the defensive alkaloids will be needed. Coccinelid beetles seem to be the sole source of the defence alkaloids. Consequently much attention has been paid to developing syntheses of these compounds. Hippodamine (1) is a naturally occurring alkaloid