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Literature summary for 4.2.3.17 extracted from

  • Jin, Y.; Williams, D.C.; Croteau, R.; Coates, R.M.
    Taxadiene synthase-catalyzed cyclization of 6-fluorogeranylgeranyl diphosphate to 7-fluoroverticillenes (2005), J. Am. Chem. Soc., 127, 7834-7842.
    View publication on PubMed

Organism

Organism UniProt Comment Textmining
Taxus brevifolia
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
7-fluorogeranylgeranyl diphosphate
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Taxus brevifolia (1R,3E,7Z,11R)-7-fluoro-4,8,12,15,15-pentamethyl-bicyclo[9.3.1]pentadeca-3,7,12-triene i.e. endo-7-fluoroverticillene, 25% yield ?
7-fluorogeranylgeranyl diphosphate
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Taxus brevifolia 4(20)-methylene-7-fluoroverticillene i.e. 4(20)-methylene-7-fluoroverticillene, 26% yield ?
7-fluorogeranylgeranyl diphosphate verticille-12-yl carbocation intermediate with an 11R stereocenter, the reaction gives three main products and two further isomers Taxus brevifolia (1S,3E,7Z,11R)-7-fluoro-4,8,15,15-tetramethyl-12-methylene-bicyclo[9.3.1]pentadeca-3,7-diene i.e. exo-7-fluoroverticillene, 37% yield ?