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An Efficient Total Synthesis of (2 E ,4 E ,7 R )‐Farnesa‐2,4,10‐triene from ( R )‐(+)‐Citronellal
Author(s) -
Li Jing,
Liu Zuosheng,
Lan Jiong,
Li Yulin
Publication year - 1999
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199900041
Subject(s) - chemistry , citronellal , total synthesis , intermolecular force , stereochemistry , sesquiterpene , hydrocarbon , monoterpene , organic chemistry , molecule , catalysis
(2 E ,4 E ,7 R )‐farnesa‐2,4,10‐triene(Caparratriene) ( 1 ), a novel sesquiterpene hydrocarbon with significant growth inhibitory activity against CEM leukemia cells, was first synthesized from ( R )‐(+)‐citronellal ( 2 ) by employing titanium‐induced intermolecular carbonyl‐coupling as the key step. The absolute configuration of (+)‐Caparratriene was determined to be 7 R.