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Mixed Superbase LICKOR as a Key Reagent for the Synthesis of Conjugate Dienes from Citral and Farnesal – A New Route to a Potential Mimic Agent of Juvenile Hormones by Diels–Alder Cycloaddition
Author(s) -
Tivola Paolo Balma,
Deagostino Annamaria,
Fenoglio Claudia,
Mella Mariella,
Prandi Cristina,
Venturello Paolo
Publication year - 1999
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/(sici)1099-0690(199909)1999:9<2143::aid-ejoc2143>3.0.co;2-c
Subject(s) - chemistry , superbase , cycloaddition , citral , regioselectivity , conjugate , diene , reagent , carbanion , diels–alder reaction , derivative (finance) , organic chemistry , combinatorial chemistry , essential oil , catalysis , mathematical analysis , natural rubber , mathematics , chromatography , financial economics , economics
Treatment of the dimethyl acetals of citral ( 1 ) and farnesal ( 2 ) with the superbase “ LICKOR ” in THF at low temperatures induces regioselective metallation at the allylic methyl group at C(3). The metal–hydrogen exchange promotes immediate 1,4‐elimination, yielding an ( E )‐configured conjugate alkyloxy‐functionalized diene. The elimination product can be subjected to a Diels–Alder reaction, which allows further synthetic elaboration. In particular, in the case of farnesal dimethyl acetal the cycloaddition process leads to a derivative that can be transformed into a potential mimic agent of Juvenile hormones.