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EC Number Reaction Commentary Reference
Display the reaction diagram Show all sequences 4.2.3.64(2E,6E)-farnesyl diphosphate + H2O = (+)-epicubenol + diphosphate - -
Display the reaction diagram Show all sequences 4.2.3.64(2E,6E)-farnesyl diphosphate + H2O = (+)-epicubenol + diphosphate the initial isomerization of farnesyl diphosphate to (3R)-nerolidyl diphosphate takes place with suprafacial stereochemistry. Ionization of (3R)-nerolidyl diphosphate and attack by the 10-11 double bond on the re face of the cisoid allylic cation-diphosphate anion pair generates the cis-germacradienyl cation. A second electrophilic cyclization gives the cadinanyl cation, which upon a 1.2-hydride shift and syn capture of water generates epicubenol -, 712232
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