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17 results on '"Louis Diorazio"'

1. Green Chemistry Articles of Interest to the Pharmaceutical Industry

Author

Alba Diaz Rodriguez, Charlotte Dalton, Louis Diorazio, Jaika Doerfler, Oliver D. Engl, Matthew Hickey, Gareth Howell, Marc Hutchby, Jonathan Latham, Wei Li, Rachel Munday, Paul Richardson, Philipp C. Roosen, Alan Steven, Jack A. Terrett, Daniel S. Treitler, Timothy White, and Mingshuo Zeng

Subjects
Organic Chemistry, Physical and Theoretical Chemistry
Published
2020
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2. Green Chemistry Articles of Interest to the Pharmaceutical Industry

Author

Marie-Gabrielle Braun, Alba Díaz-Rodríguez, Louis Diorazio, Kenneth Fraunhoffer, John Hayler, Matthew Hickey, Lucie E. Lovelle, Mark McLaws, Andrew T. Parsons, Paul Richardson, Gheorghe-Doru Roiban, Alan Steven, Jack A. Terrett, Timothy White, and Jingjun Yin

Subjects
Organic Chemistry, Physical and Theoretical Chemistry
Published
2019
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3. Green Chemistry Articles of Interest to the Pharmaceutical Industry

Author

Marian C. Bryan, Louis Diorazio, Zhongbo Fei, Kenneth Fraunhoffer, John Hayler, Matthew Hickey, Shaun Hughes, Luke Humphreys, Paul Richardson, Markus Schober, Alan Steven, Timothy White, Stijn Wuyts, and Jingjun Yin

Subjects
010405 organic chemistry, Organic Chemistry, Physical and Theoretical Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences
Published
2017
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4. Green Chemistry Articles of Interest to the Pharmaceutical Industry

Author

Rakeshwar Bandichhor, Apurba Bhattacharya, Marian C. Bryan, Louis Diorazio, Peter Dunn, Kenneth Fraunhoffer, Fabrice Gallou, John Hayler, Matthew Hickey, Luke Humphreys, Paul Richardson, Gheorghe-Doru Roiban, Timothy White, Stijn Wuyts, and Jingjun Yin

Subjects
010405 organic chemistry, Organic Chemistry, Physical and Theoretical Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences
Published
2016
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5. Green Chemistry Articles of Interest to the Pharmaceutical Industry

Author

Rakeshwar Bandichhor, Apurba Bhattacharya, Andrew Cosbie, Louis Diorazio, Peter Dunn, Kenneth Fraunhoffer, Fabrice Gallou, John Hayler, Matthew Hickey, Bill Hinkley, Luke Humphreys, Bernard Kaptein, Lynette Oh, Paul Richardson, Scott Roberts, Timothy White, Stijn Wuyts, and Jingjun Yin

Subjects
Organic Chemistry, Physical and Theoretical Chemistry
Published
2015
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6. Green Chemistry Articles of Interest to the Pharmaceutical Industry

Author

Marie-Gabrielle Braun, Louis Diorazio, Kenneth Fraunhoffer, John Hayler, Matthew Hickey, Jonathan Latham, Lucie E. Lovelle, Mark McLaws, Andrew T. Parsons, Paul Richardson, Gheorghe-Doru Roiban, Philipp C. Roosen, Alan Steven, Jack A. Terrett, Timothy White, and Jingjun Yin

Subjects
010405 organic chemistry, Organic Chemistry, Physical and Theoretical Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences
Published
2014
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7. Green Chemistry Articles of Interest to the Pharmaceutical Industry

Author

Rakeshwar Bandichhor, Apurba Bhattacharya, Louis Diorazio, Peter Dunn, Kenneth Fraunhoffer, Fabrice Gallou, John Hayler, Matthew Hickey, Bill Hinkley, David Hughes, Luke Humphreys, Bernd Janocha, Bernard Kaptein, Suju Mathew, Thomas Rammeloo, Paul Richardson, and Timothy White

Subjects
Organic Chemistry, Physical and Theoretical Chemistry
Published
2013
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8. Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement

Author

James Tarrant, Louis Diorazio, M. Giles, Philip Magnus, Philip Pye, Stephen Thom, and Timothy J. Donohoe

Subjects
Stereochemistry, Organic Chemistry, Pinacol rearrangement, Ring (chemistry), Biochemistry, chemistry.chemical_compound, chemistry, Furan, Intramolecular force, Drug Discovery, Stereoselectivity, Solvolysis, Trifluoromethanesulfonate, Enone
Abstract

The substituted furan carboxaldehyde 15 was converted into enone 20 via a stereoselective intramolecular pyrylium ylide-alkene cyclization. Subsequent elaboration of 20 into the triflate 23, followed by solvolysis in acidic trifluoroethanol resulted in quantitative rearrangement to the taxane B/C core 24. At a higher oxidation level 27 was ring expanded to give 28. The ring expansion strategy could also be initiated by β-elimination of the 3α, 10α-oxido bridge. Treatment of 50 with MeOH at reflux gave 52. Similar transformations in the 7-oxy series resulted in ring B expansion of 67 to give 68, and 75 to give 76.

Published
2016

9. NEW STRATEGY FOR THE SYNTHESIS OF THE TAXANE DITERPENES - FORMATION OF THE BC-RINGS OF TAXOL VIA A [5+2]-PYRYLIUM YLIDE-ALKENE CYCLIZATION, RING EXPANSION STRATEGY

Author

Louis Diorazio, Mark R. DeLuca, William Bauta, José Mendoza, Philip Magnus, Nicholas Magnus, Timothy J. Donohoe, John A. Booth, Philip Pye, Stephen Thom, Feroze Ujjainwalla, James Tarrant, and M. E. Bos

Subjects
chemistry.chemical_classification, Taxane, Alkene, Stereochemistry, Organic Chemistry, Ring (chemistry), Biochemistry, Cyclopropane, chemistry.chemical_compound, chemistry, Ylide, Reductive cleavage, Intramolecular force, Drug Discovery
Abstract

The BC-rings of taxol can be synthesized using an intramolecular [5+2]-pyrylium ylide-alkene cyclization, followed by gem -methylcyclopropanation and reductive cleavage of the internal cyclopropane bond.

Published
2016
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10. Taxane diterpenes .2. Synthesis of the 7-deoxy ABC taxane skeleton, and reactions of the A-ring

Author

Nicholas Magnus, José Mendoza, Louis Diorazio, John A. Booth, Philip Magnus, James Tarrant, Timothy J. Donohoe, Vincent M. Lynch, and Philip Pye

Subjects
chemistry.chemical_classification, Nitroaldol reaction, Ketone, Bicyclic molecule, Chemistry, Stereochemistry, Alkene, Organic Chemistry, Biochemistry, Nef reaction, Stereospecificity, Aldol reaction, Drug Discovery, Butenolide
Abstract

The bicyclo[5.4.0]undecenones 5, 6 and 7 are converted through a four step sequence involving activation, gem -methylcyclopropanation and reductive cleavage into the B/C rings of the taxanes, 18 and 19 . The A-ring has been attached to the B/C ring system by cyclization of the sulfone-ester 28 to give 29 , and also at a higher oxidation level; 33 gives 34 . The same type of anionic cyclization is successful in the presence of the C-1 hydroxyl group; 39 gives 40 . The A-ring can also be made using the classical aldol reaction; 43 to give 45 . A third A-ring closure method using the nitro-aldol reaction (Henry reaction) was also successful; 47 gives 48 . The A-ring has been elaborated by conversion into the tax-12, 13-enes 53 and 58 . Hydroxyl directed epoxidation of 60 results in completely stereospecific oxidation to give 61 . Autoxidation of 41 gave the 12, 13-dioxotaxane 67 which was further elaborated into the exomethylene ketone 70 . The α,β-unsaturated nitro alkene 74 has been converted into the 13-ketotaxane 76 using a reductive Nef reaction. Subsequent reduction of the C-13 carbonyl group with DIBAL-H gave the 13-α-alcohol 77 with the correct C-13 taxol stereochemistry. β-Elimination of the 3, 10-oxido bridge via the dianion of the acid 81 results in transannular hydride shift to give the butenolide 83 .

Published
2016

11. ChemInform Abstract: New Strategy for the Synthesis of the Taxane Diterpenes: Formation of the BC-Rings of Taxol via a (5 + 2) Pyrylium Ylide-Alkene Cyclization, Ring Expansion Strategy

Author

Nicholas Magnus, Philip Pye, Mark R. DeLuca, Louis Diorazio, William Bauta, José Mendoza, John A. Booth, Timothy J. Donohoe, James Tarrant, Feroze Ujjainwalla, M. E. Bos, Philip Magnus, and Stephen Thom

Subjects
chemistry.chemical_classification, Terpene, chemistry.chemical_compound, Taxane, chemistry, Ylide, Stereochemistry, Alkene, Intramolecular force, Reductive cleavage, General Medicine, Ring (chemistry), Cyclopropane
Abstract

The BC-rings of taxol can be synthesized using an intramolecular [5+2]-pyrylium ylide-alkene cyclization, followed by gem -methylcyclopropanation and reductive cleavage of the internal cyclopropane bond.

Published
2010
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12. ChemInform Abstract: New Strategy for the Synthesis of the Taxane Diterpenes: Formation of the Eight-Membered B-Ring of Taxol by Semi-Pinacol Rearrangement

Author

James Tarrant, Philip Pye, Stephen Thom, Timothy J. Donohoe, Louis Diorazio, M. Giles, and Philip Magnus

Subjects
Terpene, Taxane, Chemistry, Stereochemistry, General Medicine, Solvolysis, Ring (chemistry), Pinacol rearrangement
Abstract

Solvolysis of the neopentyl triflates 14, 25 and 32 resulted in ring expansion of a seven-membered ring into the eight-membered ring required for the synthesis of the taxanes diterpenoids.

Published
2010
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14. ChemInform Abstract: Taxane Diterpenes. Part 1. Control of Relative and Absolute Stereochemistry in Intramolecular Pyrylium Ylide-Alkene Cyclizations for the Synthesis of Taxol Precursors

Author

M. E. Bos, John A. Booth, Louis Diorazio, Philip Magnus, Feroze Ujjainwalla, José Mendoza, Nicholas Magnus, Stephen Thom, James Tarrant, Mark R. DeLuca, Christopher G. Frost, William E. Bauta, Philip Pye, and Timothy J. Donohoe

Subjects
chemistry.chemical_classification, Terpene, Taxane, chemistry, Ylide, Stereochemistry, Alkene, Intramolecular force, General Medicine
Published
2010
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16. Taxane diterpenes .1. Control of relative and absolute stereochemistry in intramolecular pyrylium ylide-alkene cyclizations for the synthesis of taxol precursors

Author

Feroze Ujjainwalla, William E. Bauta, Mark R. DeLuca, Louis Diorazio, John A. Booth, José Mendoza, Christopher G. Frost, James Tarrant, Philip Pye, Nicholas Magnus, Timothy J. Donohoe, Philip Magnus, Stephen Thom, and M. E. Bos

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, Taxane, chemistry, Bicyclic molecule, Stereochemistry, Alkene, Ylide, Intramolecular force, Organic Chemistry, Drug Discovery, Biochemistry, Methyl group
Abstract

Intramolecular pyrylium ylide-alkene cyclizations provide control of the absolute stereochemistry at the crucial C-19 angular methyl group, and leads to bicyclo[5.4.0 3,8]undecenones that contain the structral elements of the B/C rings of the taxanes.

Published
1996

17. New strategy for the synthesis of the taxane diterpenes: formation of the eight-membered B-ring of taxol by semi-pinacol rearrangement

Author

M. Giles, Stephen Thom, Louis Diorazio, Philip Magnus, James Tarrant, Philip Pye, and Timothy J. Donohoe

Subjects
Taxane, Stereochemistry, Chemistry, Molecular Medicine, Solvolysis, Pinacol rearrangement, Ring (chemistry)
Abstract

Solvolysis of the neopentyl triflates 14, 25 and 32 resulted in ring expansion of a seven-membered ring into the eight-membered ring required for the synthesis of the taxanes diterpenoids.

Published
1995
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