BIOSYNTHESIS OF (-CUBENENE AND (+)-EPICUBENOL BY CELL-FREE-EXTRACTS OF CULTURED-CELLS OF HETEROSCYPHUS-PLANUS AND CYCLIZATION OF [H-2]FARNESYL DIPHOSPHATES())

The absolute stereochemistry of cubenene and epicubenol from cultured cells of Heteroscyphus planus was determined as both (+)-isomers by H- 1 and C-13 NMR spectroscopy, GLC using a chiral capillary column, and optical rotations. Incubation of two geometrical isomers of deuteriate d farnesyl diphosphate (FPP) with a cell-free extract from cultured ce lls indicated that both compounds were specifically formed from (2E,6E )-FPP. Gas-liquid chromatography-mass spectrometry (GLC-MS) and H-2 NM R analyses of(+)-cubenene and (+)-epicubenol generated from [1,1-H-2(2 )]- and [6-H-2]-FPP confirmed the presence of 1,2- and 1,3-hydride shi fts in their formation.