1969
DOI: 10.1002/jlac.19697260124
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Darstellung von 6α‐Fluor‐16α‐methyl‐11β.21‐dihydroxy‐1.4‐pregnadien‐3.20‐dion (Fluocortolon) über eine Substrat‐Struktur‐gelenkte spezifische 11β‐Hydroxylierung mit Curvularia lunata

Abstract: Eingegangen a m 12. Februar 1969Die bei der 1 I P-Hydroxylierung von 6a-Fluor-21 -hydroxy-16a-methyl-4-pregnen-3.20-dion (9b) mit Curvularia lunata entstehenden Nebenprodukte 14 und 13 mit 9a-und 14a-HydroxyFunktion treten bei Einsatz der 5a-Brom-substituierten Vorstufe 5 durch sterische Abschirmung der a-Seite nicht auf. Der weitere Synthesegang zu 6a-Fluor-1 I ?.2l-dihydroxy-l6a-methyl-1.4-pregnadien-3.20-dion (15, Fluocortolon) wird beschrieben. Preparation of 6a-Fluoro-I 18,21 -dihydroxy-l6a-methyl-l,4-pre… Show more

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Cited by 15 publications
(2 citation statements)
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“…Fluorine acts merely as a blocking group. [31,32] Where the favored site is more remote from the fluorine substituent(s), the behavior of a fluoro compound resembles that of its parent. [32] Holland et al observed different enantioselectivity for the monohydroxylation of o-, m-, or p-fluorinated ethylbenzenes by Mortierella isabellina.…”
Section: Methodsmentioning
confidence: 90%
See 1 more Smart Citation
“…Fluorine acts merely as a blocking group. [31,32] Where the favored site is more remote from the fluorine substituent(s), the behavior of a fluoro compound resembles that of its parent. [32] Holland et al observed different enantioselectivity for the monohydroxylation of o-, m-, or p-fluorinated ethylbenzenes by Mortierella isabellina.…”
Section: Methodsmentioning
confidence: 90%
“…Thus, substitution of the 6α-position in 21-hydroxy-16α-methyl-4-pregnene-3,20-dione by fluorine blocks the unwanted 7β-hydroxylation by Curvularia lunata, redirecting hydroxylation to the 11α-or the 9α-position. [31] Several more monofluoro-and gem-difluoro-5a-androstanones and the parent ketones have been transformed with different fungi such as Aspergillus ochra-ceus. With few exceptions, hydroxylation is diverted to an alternative position neither at nor adjacent to the carbon atom to which a fluorine atom is attached, even though one of these centers in the parent compound is a favored site.…”
Section: Methodsmentioning
confidence: 99%