Chemical-Microbiological Synthesis of Cryptomeridiol Derivatives by <i>Gliocladium </i><i>r</i><i>oseum</i>:  Semisynthesis of 11-Hydroxyeudesmanolides Andrés García-Granados María C. Gutiérrez Andrés Parra Francisco Rivas 10.1021/np010631m.s001 https://acs.figshare.com/articles/journal_contribution/Chemical-Microbiological_Synthesis_of_Cryptomeridiol_Derivatives_by_i_Gliocladium_i_i_r_i_i_oseum_i_Semisynthesis_of_11-Hydroxyeudesmanolides/3734232 Biotransformations of 4α- and 4β-hydroxyeudesmane derivatives by the filamentous fungus <i>Gliocladium roseum</i> were achieved. Hydroxylation at C-11 was the main action of this microorganism, producing new cryptomeridiol (<b>12</b> and <b>14</b>) and 4-<i>epi</i>-cryptomeridiol derivatives (<b>6</b> and <b>7</b>), respectively, in good yields. The biotransformation activity of <i>G. roseum</i> toward 4β-hydroxyeudesmane was focused on the isopropyl moiety, but more scattered on the 4α-hydroxylated derivative, acting in both the “A” and “B” rings and the isopropyl group of the molecule. Semisyntheses of 11-hydroxyeudesmanolides from the isolated 11,12-dihydroxylated metabolites were also accomplished and used in assigning the stereochemistry of hydroxylation. 2002-07-03 00:00:00 isopropyl group Hydroxyeudesmanolide microorganism Hydroxylation cryptomeridiol derivatives metabolite dihydroxylated hydroxyeudesmane Semisynthesi hydroxylated filamentous fungus Gliocladium roseum Synthesi biotransformation activity hydroxyeudesmanolide molecule yield hydroxylation Biotransformation stereochemistry Semisynthese Cryptomeridiol Derivatives isopropyl moiety epi