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Stereoselective Synthesis of ( E )‐Tagetone
Author(s) -
Kunz Joachim,
Breitmaier Eberhard
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199504102
Subject(s) - chemistry , wittig reaction , alkylation , aldehyde , yield (engineering) , stereoselectivity , sulfuric acid , dithiane , organic chemistry , medicinal chemistry , catalysis , materials science , metallurgy
( E )‐Tagetone ( 8 ) was prepared in four steps by successive alkylation of 1,3‐dithiane ( 1 ) by 1‐iodo‐2‐methylpropane ( 2 ) and by 3‐ethoxy‐2‐methylacrolein ( 3 ), followed by treatment of the intermediate 4 with sulfuric acid. Wittig alkylenation of the resulting aldehyde 5 and removal of the protecting group affords the title compound in good yield.