REGIOSELECTIVE OXYFUNCTIONALIZATION OF BRASSINOSTEROIDS BY METHYL(TRIFLUOROMETHYL)DIOXIRANE - SYNTHESIS OF 25-HYDROXY-BRASSINOLIDE AND 25-HYDROXY-24-EPIBRASSINOLIDE BY DIRECT C-H INSERTION

Authors
VOIGT B PORZEL A GOLSCH D ADAM W ADAM G
Citation
B. Voigt et al., REGIOSELECTIVE OXYFUNCTIONALIZATION OF BRASSINOSTEROIDS BY METHYL(TRIFLUOROMETHYL)DIOXIRANE - SYNTHESIS OF 25-HYDROXY-BRASSINOLIDE AND 25-HYDROXY-24-EPIBRASSINOLIDE BY DIRECT C-H INSERTION, Tetrahedron, 52(32), 1996, pp. 10653-10658
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
32
Year of publication
1996
Pages
10653 - 10658
Database
ISI
SICI code
0040-4020(1996)52:32<10653:ROOBBM>2.0.ZU;2-I
Abstract
The direct oxyfunctionalization of suitable brassinosteroid derivative s at position 25 using methyl(trifluoromethyl)dioxirane is reported. W hereas reaction with tetraacetyl brassinolide led after deprotection d irectly to the desired 25-hydroxy-brassinolide, in the (24R) series th e 22,23-isopropylidenedioxy derivative has been shown to be a suitable precursor for the 25-hydroxylation leading to 25-hydroxy-24-epicastas terone and upon Baeyer-Villiger oxidation to 25-hydroxy-24-epibrassino lide, respectively. Copyright (C) 1996 Elsevier Science Ltd