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Direct and Short Construction of the ACDE Ring System of Daphenylline
Author(s) -
Wang Wei,
Li GuoPing,
Wang ShaoFeng,
Shi ZiFa,
Cao XiaoPing
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403152
Subject(s) - stereocenter , ring (chemistry) , intramolecular force , alkene , acylation , chemistry , aryl , yield (engineering) , stereochemistry , organic chemistry , catalysis , materials science , enantioselective synthesis , alkyl , metallurgy
Daphenylline, a novel daphniphyllum alkaloid, boasts a fused and bridging ring system coupled with six stereogenic centers. Here we present a direct and short construction of the ACDE ring system of daphenylline from the known 3‐(2‐bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)‐catalyzed aza‐Cope‐Mannich reaction, a self‐terminating 6‐ exo‐trig aryl radical‐alkene cyclization and an intramolecular Friedel–Crafts acylation.