Allylic Oxidation of some 5,6‐Unsaturated Steroids with Lead Tetraacetate. Communication XXII on reactions with lead tetraacetate

Stefanović, Milena; Jokić, Aleksandar; Maksimović, Zoran; Lorenć, Lj.; Mihailović, M. Lj.

doi:10.1002/hlca.19700530740

Cited by 11 publications

(3 citation statements)

References 13 publications

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“…[15][16][17] We have been developing a 7a-hydroxylation system for steroids, [18][19][20] and we reported in a preceding paper that the combination of electrolysis and the Fe III (PA) 3 /O 2 /CH 3 CN system gave good results in the hydroxylation of cholesteryl acetate. 21) On the other hand, functionalization, especially oxygenation, of octahydronaphthalenes or decalin derivatives is also very important because many bioactive or natural compounds contain a skeleton resembling the AB fused ring of cholesterol.…”

Section: IIImentioning

confidence: 99%

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Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes

Okamoto

Funaki

Nobuchika

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Oxygenation reactions are very important in steroid metabolism and biosynthesis.1-3) Many investigations on biomimetic oxygenation systems using iron(III) picolinate (Fe III (PA) 3 ) or iron(II) picolinate (Fe II (PA) 2 ) complexes as catalysts have been reported under various conditions and in various solvents, [4][5][6][7][8] but direct 7a-hydroxylation is not easy and most reported allylic hydroxylations involve multistep reactions via other functionalized compounds [9][10][11][12][13][14] or afford low yield or stereoselectivity. [15][16][17] We have been developing a 7a-hydroxylation system for steroids, [18][19][20] and we reported in a preceding paper that the combination of electrolysis and the Fe III (PA) 3 /O 2 /CH 3 CN system gave good results in the hydroxylation of cholesteryl acetate. 21)On the other hand, functionalization, especially oxygenation, of octahydronaphthalenes or decalin derivatives is also very important because many bioactive or natural compounds contain a skeleton resembling the AB fused ring of cholesterol.22-24) Therefore, we wished to identify the required structural factors for regio-and stereoselective direct 7a-hydroxylation of steroids by our electrochemical method, as well as to extend the range of applicability of this method for allylic a-hydroxylation of small cyclic compounds.In this report, we describe the iron picolinate-induced hydroxylation reactions of octahydronaphthalene derivatives 5b, 6b and 7b as simple models for allylic oxygenation of steroids or other decalin derivatives. Results and DiscussionThe substrates 5b-7b were prepared by benzoylation of the corresponding octahydronaphthalenols 5a-7a. [25][26][27] Both 5b and 6b have an alkene moiety at a similar position to C5-C6 of cholesterol. However, the double bond of 7b is not located at the bridgehead of the fused ring. We applied Showa Pharmaceutical University; 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan. Received October 23, 2004; accepted November 11, 2004; published online November 22, 2004 The combination of electrolysis and the Fe III (PA) 3 /O 2 /CH 3 CN system was investigated for allylic hydroxylation of octahydronaphthalene derivatives. Substrates with a bridgehead double bond gave the allylic alcohol with a a-preference, while non-bridgehead olefin did not react smoothly. This system is a useful tool for a a-selective allylic hydroxylation of octahydronaphthalene derivatives with a bridgehead double bond as model compounds for the AB fused ring of cholesterols.

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Section: IIImentioning

confidence: 99%

mentioning

confidence: 99%

Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes

Okamoto

Funaki

Nobuchika

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Genus Ambrosia L. 3.2.1. Ambrosia artemisiifolia L. (the common rag weed)The plant material (aerial parts) of A. artemisiifolia was collected at two localities in the Province of Vojvodina, i.e., near Novi Sad (October 1970)7,51,83 and near Pan~evo (August 1983).…”

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Sesquiterpene lactones from the Yugoslavian wild growing plant families asteraceae and apiaceae

Milosavljević

Bulatovic

Stefanović

1999

JSCS

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1. Introduction 2. Results 3. Asteraceae 3.1. Genus Artemisia L. 3.1.1. Artemisia annua L. 3.1.2. Artemisia vulgaris L. 3.1.3. Artemisia absinthium L. (warmwood) 3.1.4. Artemisia scoparia W. et K. 3.1.5. Artemisia camprestris L. 3.2. Genus Ambrosia L. 3.2.1. Ambrosia artemisiifolia L. (the common rag weed) 3.3. Genus Tanacetum L. ( syn. Chrysanthemum L.) 3.3.1. Tanacetum parthenium L. (feverfew) 3.3.2. Tanacetum serotinum L. 3.3.3. Tanacetum vulgare L. (tansy) 3.3.4. Tanacetum macrophyllum Willd. 3.3.5. Tanacetum corymbosum L. 3.4. Genus Telekia Baumg. 3.4.1. Telekia speciosa (Schreb.) Baumg. 3.5. Genus Inula L. 3.5.1. Inula helenium L. 3.5.2. Inula spiraeifolia L. 3.6. Genus Eupatorium L. 3.6.1. Eupatorium cannabinum L. 3.7. Genus Achillea L. 3.7.1. Achillea abrotanoides Vis. 3.7.2. Achillea millefolium subsp. pannonica 3.7.3. Achillea crithmifolia W. et K. 3.7.4. Achillea clypeolata Sibth. et Sm. 3.7.5. Achillea serbica Nyman 3.7.6. Achillea depressa Janka 3.8. Genus Anthemis L. 3.8.1. Anthemis carpatica Willd. 3.8.2. Anthemis cretica L. subsp. cretica 3.9. Genus Centaurea L. 3.9.1. Centaurea derventana Vis. et Pan~. 3.9.2. Centaurea kosaninii Hayek 3.9.3. Centaurea solstitialis L. 4. Apiaceae 4.1. Genus Laserpitium L. 4.1.1. Laserpitium siler L. 4.1.2. Laserpitium marginatum L. 4.1.3. Laserpitium latifolium L. 4.1.4. Laserpitium alpinum W. K. 4.2. Genus Angelica L. 4.2.1. Angelica silvestris L. 4.3. Genus Peucedanum L. 4.3.1. Peucedanum austriacum (Jacq.) Koch

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Lead tetraacetate (LTA)

Ho¹,

Fieser²,

Fieser³

et al. 2006

Fieser and Fieser's Reagents for Organic Synthesis

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Allylic Oxidation of some 5,6‐Unsaturated Steroids with Lead Tetraacetate. Communication XXII on reactions with lead tetraacetate

Cited by 11 publications

References 13 publications

Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes

Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes

Sesquiterpene lactones from the Yugoslavian wild growing plant families asteraceae and apiaceae

Lead tetraacetate (LTA)

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