(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
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(2S,3R,6S,9S)-(-)-protoillud-7-ene i.e. (2aS,4aS,7aS,7bR)-3,6,6,7b-tetramethyl-2,2a,4a,5,6,7,7a,7b-octahydro-1H-cyclobuta[e]indene
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(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
one possible function of volatile terpenes emitted from Dictyostelium discoideum is to attract other organisms to facilitate spore dispersal, resembling the function of volatile terpenes from the fruiting bodies of fungi
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(2E,6E)-farnesyl diphosphate
(2S,3R,6S,9S)-(-)-protoillud-7-ene + diphosphate
no activity with geranyl diphosphate and geranylgeranyl diphosphate. The biosynthesis of (2S,3R,6S,9S)-(-)-protoillud-7-ene starts by 1,11-cyclization of (2E,6E)-farnesyl diphosphate to the humulyl cation. A 1,2-hydride shift and cyclization furnishes the protoilludyl cation that yields (2S,3R,6S,9S)-(-)-protoillud-7-ene upon deprotonation, while pentalenene is formed by dyotropic rearrangement and deprotonation
the major product is the sequiterpene (2S,3R,6S,9S)-()-protoillud-7-ene. Traces of pentalenene are also formed. (2S,3R,6S,9S)-()-protoillud-7-ene i.e. (2aS,4aS,7aS,7bR)-3,6,6,7b-tetramethyl-2,2a,4a,5,6,7,7a,7b-octahydro-1H-cyclobuta[e]indene
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