Synthesis of (E,E)-tricyclohexaprenol by reactive barium-promoted coupling of a geranyl- and an isocopalenyl moiety

Synlett

Volumn , Issue 16, 2005, Pages 2534-2536

  Raeppel, Franck ^a   Heissler, Denis ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Addition reactions; Allylations; Barium; Cross coupling; Terpenoids

Indexed keywords

8 GERANYLBARIUM CHLORIDE; BARIUM; GERANIOL; HEXANOL; TRICYCLOHEXAPRENOL; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE;

ADDITION REACTION; ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REDUCTION; SYNTHESIS;

EID: 26844573954     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917090     Document Type: Article

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18. 13C NMR (75 MHz): δ = 15.1, 15.7, 18.5, 18.7, 21.6, 21.7, 22.6, 33.1, 33.4, 37.2, 37.3, 39.8, 41.0, 41.9, 43.1, 54.8, 56.1, 58.1, 123.8, 132.2.
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21. 13C NMR (125 MHz): δ = 14.3, 15.5, 16.1, 16.3, 18.5, 18.8, 21.7, 22.1, 22.8, 25.7, 26.2, 33.1, 33.4, 36.8, 37.2, 39.5, 39.8, 40.6, 41.9, 42.2, 54.7, 55.1, 56.3, 59.4, 122.0, 123.3, 123.9, 135.3, 136.0, 139.8.
22. 2O, and worked up.
23. Ratio measured by GC. The E/Z-isomerization could have occurred either in the allylic barium reagent or during the reduction of the xanthate, which proceeds via a homoallylic radical.
24. 2O, 93:7, v/v. Flow rate: 30 mL/min.
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