ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Microbiological Hydroxylation of 5α.6α-Epoxy-3β-hydroxy-5α-pregnane-20-ones with further TransformationsThe fungus Curvularia lunata transforms in prolongated incubation time 5α.6α; 16α.17α-diepoxy-3β-hydroxy-5α-pregnane-20-one (1) to the 5β-H-6-ketone 3 and 4 through the primarily formed 11β-hydroxy-structure 2. 5α.6α-Epoxy-3β-hydroxy-5α-pregnane-20-one (6) is oxidized to 14α- or 17α-hydroxy-11-ketones (8-10, 12). During this reaction a change of the substitution pattern of the rings A and B is sometimes observed. The corresponding 16α-methyl-substituted substrate 14 is transformed through some intermediates to the stable product 5α.6α-epoxy-3β.15β-dihydroxy-16α-methyl-5α-pregnane-11.20-dione (18). The constitutions of the isolated compounds were elucidated by n.m.r., i.r., mass spectroscopic, and c.d. investigations.
Notes:
Der Pilz Curvularia lunata wandelt 3β-Hydroxy-5α.6α; 16α.17α-diepoxy-5α-pregnanon-(20) (1) bei verlängerter Inkubationszeit über die primär entstehende 11β-Hydroxystruktur 2 in die 5β-H-6-Ketone 3 und 4 um. 3β-Hydroxy-5α.6α-epoxy-5α-pregnanon-(20) (6) wird zu 14α-oder 17α-Hydroxy-11-ketonen (8-10, 12) oxydiert, wobei gleichzeitig noch eine Änderung des Substitutionsmusters am A- und B-Ring eintreten kann, während die entsprechende 16α-Methylverbindung 14 über verschiedene Zwischenstufen zum stabilen Endprodukt 3β.15β-Di-hydroxy-5α.6α-epoxy-16α-methyl-5α-pregnandion-(11.20) (18) transformiert wird. Die Konstitutionen der isolierten Verbindungen wurden durch NMR-, IR-, MS- und CD-Untersuchungen gesichert.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19721050232
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