The invention of new radical chain reactions. part X1 1 Part IX, D.H.R. Barton, D. Crich and G. Kretzschmar, J. Chem. Soc. (Perkin 1) in press. High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy-vitamin D3 side chain from bi

Derek H.R. Barton; Hideo Togo; Samir Z. Zard

doi:10.1016/S0040-4020(01)91351-1

The invention of new radical chain reactions. part X¹ 1 Part IX, D.H.R. Barton, D. Crich and G. Kretzschmar, J. Chem. Soc. (Perkin 1) in press. High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy-vitamin D₃ side chain from bi

Derek H.R. Barton
, Hideo Togo
, Samir Z. Zard

Institut de Chimie des Substances Naturelles

Research output: Contribution to journal › Article › peer-review

Abstract

Radicals derived from thiohydroxamic esters 3 readily add to nitroolefins 5 (Z = NO₂) to give good yields of α-nitrosulphides. These adducts, where the structure permits, are easily oxidised to carboxylic acids 8 by treatment with alkaline hydrogen peroxide. Reductive cleavage to the corresponding aldehydes or ketones 9 is efficiently carried out by the action of TiCl₃. Addition of methyl magnesium iodide to the methyl ketone derived from 3α-acetoxy 11-oxo cholanic acid gives steroid 10 possessing the 25-hydroxycholesterol side chain of the vitamin D₃ metabotites. Radical additions to 1-phenylthio-2-nitropropene 11 have been briefly studied.

Original language	English
Pages (from-to)	5507-5516
Number of pages	10
Journal	Tetrahedron
Volume	41
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4020(01)91351-1
Publication status	Published - 1 Jan 1985
Externally published	Yes

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Barton, D. H. R., Togo, H., & Zard, S. Z. (1985). The invention of new radical chain reactions. part X¹ 1 Part IX, D.H.R. Barton, D. Crich and G. Kretzschmar, J. Chem. Soc. (Perkin 1) in press. High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy-vitamin D₃ side chain from bi. Tetrahedron, 41(23), 5507-5516. https://doi.org/10.1016/S0040-4020(01)91351-1

Barton, Derek H.R. ; Togo, Hideo ; Zard, Samir Z. / The invention of new radical chain reactions. part X¹ 1 Part IX, D.H.R. Barton, D. Crich and G. Kretzschmar, J. Chem. Soc. (Perkin 1) in press. High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy-vitamin D₃ side chain from bi. In: Tetrahedron. 1985 ; Vol. 41, No. 23. pp. 5507-5516.

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title = "The invention of new radical chain reactions. part X1 1 Part IX, D.H.R. Barton, D. Crich and G. Kretzschmar, J. Chem. Soc. (Perkin 1) in press. High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy-vitamin D3 side chain from bi",

abstract = "Radicals derived from thiohydroxamic esters 3 readily add to nitroolefins 5 (Z = NO2) to give good yields of α-nitrosulphides. These adducts, where the structure permits, are easily oxidised to carboxylic acids 8 by treatment with alkaline hydrogen peroxide. Reductive cleavage to the corresponding aldehydes or ketones 9 is efficiently carried out by the action of TiCl3. Addition of methyl magnesium iodide to the methyl ketone derived from 3α-acetoxy 11-oxo cholanic acid gives steroid 10 possessing the 25-hydroxycholesterol side chain of the vitamin D3 metabotites. Radical additions to 1-phenylthio-2-nitropropene 11 have been briefly studied.",

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Barton, DHR, Togo, H & Zard, SZ 1985, 'The invention of new radical chain reactions. part X¹ 1 Part IX, D.H.R. Barton, D. Crich and G. Kretzschmar, J. Chem. Soc. (Perkin 1) in press. High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy-vitamin D₃ side chain from bi', Tetrahedron, vol. 41, no. 23, pp. 5507-5516. https://doi.org/10.1016/S0040-4020(01)91351-1

The invention of new radical chain reactions. part X¹ 1 Part IX, D.H.R. Barton, D. Crich and G. Kretzschmar, J. Chem. Soc. (Perkin 1) in press. High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy-vitamin D₃ side chain from bi. / Barton, Derek H.R.; Togo, Hideo; Zard, Samir Z.
In: Tetrahedron, Vol. 41, No. 23, 01.01.1985, p. 5507-5516.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

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PY - 1985/1/1

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AB - Radicals derived from thiohydroxamic esters 3 readily add to nitroolefins 5 (Z = NO2) to give good yields of α-nitrosulphides. These adducts, where the structure permits, are easily oxidised to carboxylic acids 8 by treatment with alkaline hydrogen peroxide. Reductive cleavage to the corresponding aldehydes or ketones 9 is efficiently carried out by the action of TiCl3. Addition of methyl magnesium iodide to the methyl ketone derived from 3α-acetoxy 11-oxo cholanic acid gives steroid 10 possessing the 25-hydroxycholesterol side chain of the vitamin D3 metabotites. Radical additions to 1-phenylthio-2-nitropropene 11 have been briefly studied.

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Barton DHR, Togo H, Zard SZ. The invention of new radical chain reactions. part X¹ 1 Part IX, D.H.R. Barton, D. Crich and G. Kretzschmar, J. Chem. Soc. (Perkin 1) in press. High yield radical addition reactions of αβ-unsaturated nitroolefins. An expedient construction of the 25-hydroxy-vitamin D₃ side chain from bi. Tetrahedron. 1985 Jan 1;41(23):5507-5516. doi: 10.1016/S0040-4020(01)91351-1