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