Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom