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Total Synthesis of (±)‐Scopolamine: Challenges of the Tropane Ring
Author(s) -
Nocquet PierreAntoine,
Opatz Till
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501430
Subject(s) - tropane , chemistry , scopolamine , cycloaddition , ring (chemistry) , stereochemistry , organic chemistry , catalysis , pharmacology , medicine
Scopolamine was synthesized using 6,7‐dehydrotropine as a key intermediate. Rhodium‐catalyzed [4 + 3] cycloaddition chemistry and a modified Robinson–Schöpf reaction were each independently evaluated for their utility in constructing the tropane core. Both synthetic approaches gave comparable overall yields.