Oxidation of natural targets by dioxiranes. 2. Direct hydroxylation at the side chain C-25 of cholestane derivatives and of vitamin D3 Windaus-Grundmann ketone
The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and 5-alpha,6-beta-Br2-3-beta-acetoxycholestane as well as of the vitamin D3-derived Windaus-Grundmann ketone has been achieved under mild conditions employing either dim...
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Published in | Journal of organic chemistry Vol. 57; no. 19; pp. 5052 - 5054 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.09.1992
Amer Chemical Soc |
Subjects | |
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Abstract | The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and 5-alpha,6-beta-Br2-3-beta-acetoxycholestane as well as of the vitamin D3-derived Windaus-Grundmann ketone has been achieved under mild conditions employing either dimethyldioxirane or its trifluoromethyl analogue. |
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AbstractList | The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and 5-alpha,6-beta-Br2-3-beta-acetoxycholestane as well as of the vitamin D3-derived Windaus-Grundmann ketone has been achieved under mild conditions employing either dimethyldioxirane or its trifluoromethyl analogue. |
Author | Curci, Ruggero Bovicelli, Paolo Prencipe, Teresa Mincione, Enrico Lupattelli, Paolo |
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Keywords | METHYL(TRIFLUOROMETHYL)DIOXIRANE ACID ACETONE POTASSIUM CAROATE INTERMEDIATE 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL DIMETHYLDIOXIRANE EPOXIDATION |
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References_xml | – volume: 2 start-page: CH1 year: 1990 ident: WOS:A1992JN95000004.15 publication-title: ADV OXYGENATED PROCE contributor: fullname: CURCI R – start-page: 203 year: 1974 ident: WOS:A1974S401300010 article-title: CONVENIENT SYNTHESIS OF CRYSTALLINE 1ALPHA,25-DIHYDROXYVITAMIN-D3 publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: BARTON, DHR – volume: 49 start-page: 371 year: 1980 ident: WOS:A1992JN95000004.47 publication-title: RUSS CHEM REV contributor: fullname: YAKHIMOVICH RI – year: 1992 ident: WOS:A1992JN95000004.45 publication-title: TOPICS NATURAL PRODU contributor: fullname: WILSON SR – volume: 52 start-page: 699 year: 1987 ident: WOS:A1987G276400045 article-title: O-17 AND C-13 IDENTIFICATION OF THE DIMETHYLDIOXIRANE INTERMEDIATE ARISING IN THE REACTION OF POTASSIUM CARBONATE WITH ACETONE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CASSIDEI, L – volume: 32 start-page: 533 year: 1991 ident: WOS:A1991EV62200029 article-title: DIOXIRANE MEDIATED STEROIDAL ALKENE EPOXIDATIONS AND OXYGEN INSERTION INTO CARBON-HYDROGEN BONDS publication-title: TETRAHEDRON LETTERS contributor: fullname: MARPLES, BA – ident: WOS:A1992JN95000004.26 publication-title: IN PRESS contributor: fullname: KUCK D – volume: 524 start-page: 295 year: 1936 ident: WOS:000200667500015 article-title: The constitution of the vitamin D publication-title: JUSTUS LIEBIGS ANNALEN DER CHEMIE contributor: fullname: Windaus, A – volume: 55 start-page: 6105 year: 1990 ident: WOS:A1990EL80200014 article-title: REGIOSPECIFIC OXIDATION OF BINOR-S AND ACID-CATALYZED REARRANGEMENT OF THE PRODUCT TO THE 1ST EXAMPLE OF A PENTACYCLO[6.6.0.05,14.07,12.09,13]TETRADECANE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: PRAMOD, K – volume: 8 start-page: 183 year: 1981 ident: WOS:A1981LT02400001 article-title: CHROMATOGRAPHIC PROPERTIES AND MASS-SPECTROMETRIC FRAGMENTATION OF DIOXYGENATED C27-STEROIDS, C28-STEROIDS, C29-STEROIDS publication-title: BIOMEDICAL MASS SPECTROMETRY contributor: fullname: ARINGER, L – volume: 111 start-page: 6749 year: 1989 ident: WOS:A1989AM21600039 article-title: OXIDATIONS BY METHYL(TRIFLUOROMETHYL)DIOXIRANE .2. OXYFUNCTIONALIZATION OF SATURATED-HYDROCARBONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MELLO, R – volume: 113 start-page: 7031 year: 1991 ident: WOS:A1991GD30600049 article-title: RELATIVE OXYGEN DONOR POTENTIAL OF DIOXIRANE AND CARBONYL OXIDE - A THEORETICAL-STUDY publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BACH, RD – volume: 114 start-page: 659 year: 1992 ident: WOS:A1992GZ44100036 article-title: SYNTHESIS OF A CYANOBACTERIAL SULFOLIPID - CONFIRMATION OF ITS STRUCTURE, STEREOCHEMISTRY, AND ANTI-HIV-1 ACTIVITY publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: GORDON, DM – volume: 56 start-page: 5480 year: 1991 ident: WOS:A1991GD34600058 article-title: DIVERGENT RESPONSE OF A HINDERED CYCLOPROPENE TO STRONG OXIDIZING-AGENTS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: MAYNARD, GD – volume: 57 start-page: 2007 year: 1992 ident: WOS:A1992HL66000021 article-title: 2 NEW APPROACHES TO THE 25-HYDROXY-VITAMIN-D2 SIDE-CHAIN publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: WILSON, SR – volume: 47 start-page: 2670 year: 1982 ident: WOS:A1982NT76600033 article-title: STEREOSELECTIVITIES AND REGIOSELECTIVITIES IN THE EPOXIDATION OF SOME ALLYLIC ALCOHOLS BY THE DIOXIRANE INTERMEDIATE GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH ACETONE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CICALA, G – volume: 41 start-page: 2651 year: 1976 ident: WOS:A1976BY49200035 article-title: HYDROXYLATION WITH OZONE ON SILICA-GEL - SYNTHESIS OF 1 ALPHA,25-DIHYDROXYVITAMIN-D3 publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: COHEN, Z – volume: 90 start-page: 664 year: 1957 ident: WOS:A1957WK07100002 article-title: STUDIEN IN DER VITAMIN D-REIHE .21. HYDRINDAN-VERBINDUNGEN AUS VITAMIN-D3 publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: INHOFFEN, HH – start-page: 1642 year: 1978 ident: WOS:A1978GD27600035 article-title: STEROIDS .209. FORMATION OF 6BETA-BROMO-5-CHLORO-5ALPHA-CHOLESTAN-3BETA-OL ON ADDITION OF BROMINE CHLORIDE TO CHOLESTEROL publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: KASAL, A – volume: 44 start-page: 2318 year: 1979 ident: WOS:A1979HA13200073 article-title: DRY OZONATION OF STEROIDS - C-25 FUNCTIONALIZATION OF CHOLESTANE DERIVATIVES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: COHEN, Z – volume: 51 start-page: 3098 year: 1986 ident: WOS:A1986D581900004 article-title: STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BAGGIOLINI, EG – volume: 45 start-page: 4758 year: 1980 ident: WOS:A1980KQ10000040 article-title: EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CURCI, R – start-page: 4147 year: 1972 ident: WOS:A1972N536100028 article-title: SYNTHESIS OF 1 ALPHA, 25-DIHYDROXYCHOLECALCIFEROL - METABOLICALLY ACTIVE FORM OF VITAMIN-D3 publication-title: TETRAHEDRON LETTERS contributor: fullname: SEMMLER, EJ – volume: 54 start-page: 271 year: 1989 ident: BCI:BCI198988134690 article-title: SYNTHESIS OF 9-ALPHA HYDROXYSTEROIDS BY A RHODOCOCCUS-SP publication-title: Steroids contributor: fullname: DATCHEVA V K – start-page: 1482 year: 1940 ident: WOS:000188176800009 article-title: Studies in the sterol group Part XLII The constitution of zymosterol publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: Heath-Brown, B – volume: 50 start-page: 2847 year: 1985 ident: WOS:A1985ANU7200007 article-title: DIOXIRANES - SYNTHESIS AND REACTIONS OF METHYLDIOXIRANES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: MURRAY, RW – start-page: 1695 year: 1977 ident: WOS:A1977DF90600005 article-title: EFFICIENT SYNTHESIS OF 25-HYDROXYCHOLESTEROL FROM STIGMASTEROL publication-title: TETRAHEDRON LETTERS contributor: fullname: SALMOND, WG – volume: 47 start-page: 1291 year: 1991 ident: WOS:A1991EX88700018 article-title: USE OF DIMETHYLDIOXIRANE IN THE PREPARATION OF EPOXY DERIVATIVES RELATED TO INSECT JUVENILE HORMONES publication-title: TETRAHEDRON contributor: fullname: MESSEGUER, A – start-page: 28 year: 1992 ident: WOS:A1992HD01000015 article-title: PREPARATION OF 9-ALPHA-HYDROXYESTRA-1,3,5(10)-TRIENES BY DIRECT BENZYLIC OXIDATION WITH DIMETHYLDIOXIRANE publication-title: JOURNAL OF CHEMICAL RESEARCH-S contributor: fullname: BROWN, DS – volume: 53 start-page: 3450 year: 1988 ident: WOS:A1988P367100009 article-title: NOVEL CONVERGENT SYNTHESIS OF SIDE-CHAIN-MODIFIED ANALOGS OF 1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: KUTNER, A – volume: 53 start-page: 3890 year: 1988 ident: WOS:A1988P689500053 article-title: ON THE ISOLATION AND CHARACTERIZATION OF METHYL(TRIFLUOROMETHYL)DIOXIRANE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: MELLO, R – volume: 22 start-page: 205 year: 1989 ident: WOS:A1989AB90300002 article-title: DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS publication-title: ACCOUNTS OF CHEMICAL RESEARCH contributor: fullname: ADAM, W – volume: 56 start-page: 5448 year: 1991 ident: WOS:A1991GD34600047 article-title: A STEREOSPECIFIC ROUTE TO 2-DEOXY-BETA-GLYCOSIDES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: GERVAY, J – volume: 325 start-page: 422 year: 1983 ident: WOS:A1983RC87100010 article-title: C-13-NMR SPECTROSCOPIC INVESTIGATIONS OF BROMINATED 3-KETO-5-ALPHA-CHOLESTANE AND 3-BETA-ACETOXY-5-ALPHA-CHOLESTANE DERIVATIVES publication-title: JOURNAL FUR PRAKTISCHE CHEMIE contributor: fullname: ROMER, J – volume: 89 start-page: 1187 year: 1989 ident: WOS:A1989AK60600014 article-title: CHEMISTRY OF DIOXIRANES .12. DIOXIRANES publication-title: CHEMICAL REVIEWS contributor: fullname: MURRAY, RW – volume: 32 start-page: 6057 year: 1991 ident: WOS:A1991GL92700002 article-title: CHEMICAL CONVERSION OF VITAMIN-D3 TO ITS 1,25-DIHYDROXY METABOLITE publication-title: TETRAHEDRON LETTERS contributor: fullname: KIEGIEL, J – volume: 75 start-page: 5421 year: 1953 ident: WOS:A1953UB53400089 article-title: CHOLESTEROL AND COMPANIONS .7. STEROID DIBROMIDES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: FIESER, LF – volume: 56 start-page: 7292 year: 1991 ident: WOS:A1991GW89100020 article-title: EPOXIDATION OF FLAVONES BY DIMETHYLDIOXIRANE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: ADAM, W – volume: 114 start-page: 1346 year: 1992 ident: WOS:A1992HD97800032 article-title: DIOXIRANES .20. 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Snippet | The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and... |
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SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | Oxidation of natural targets by dioxiranes. 2. Direct hydroxylation at the side chain C-25 of cholestane derivatives and of vitamin D3 Windaus-Grundmann ketone |
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