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19 results on '"Bertinato, Peter"'

1. Total syntheses of epothilones A and

Author

Meng, Dongfang, Bertinato, Peter, Balog, Aaron, Su, Dai-Shu, Kamenecka, Ted, Sorensen, Erik J., and Danishefsky, J.

Subjects
Stereochemistry -- Usage, Organic compounds -- Synthesis, Macrolide antibiotics -- Research, Chemistry
Abstract

Experiments on the assembly of epothilone systems led to the convergent and stereocontrolled total synthesis of the microtubule-stabilizing macrolides epothilones A and B through ring-forming strategies. The constructions involve union at either the C11-C12 bond or the C12-13 bond. All stereochemistry is induced from the single chiral center with C8 incorporated into the dynamic. This method allows strict control over the geometry of the double bonds of the epothilones through adaptions of the B-alkyl Suzuki reactions.

Published
1997

3. Remote effects in macrolide formation through ring-forming olefin metathesis: an application to the synthesis of fully active epothilone congeners

Author

Meng, Dongfang, Su, Dai-Shi, Balog, Aaron, Bertinato, Peter, Sorensen, Erik J., Danishefsky, Samuel J., Zheng, Yu-Huang, Chou, Ting-Chao, He, Lifeng, and Horwitz, Susan B.

Subjects
Macrolide antibiotics -- Research, Olefins -- Research, Chemistry
Abstract

A novel technique involving the ring-forming olefin metathesis reaction for the construction of the C12-C13 bond was used for generating desoxyepothilone. The results confirmed that ROM chemistry can be applied for the synthesis of fully active epothilone congeners. It is proposed that the same method can have wider application for the construction of other highly biologically active congeners.

Published
1997

4. Studies toward a synthesis of epothilone A: stereocontrolled assembly of the acyl region and models for macrocyclization

Author

Bertinato, Peter, Sorensen, Erik J., Meng, Dongfang, and Danishefsky, Samuel J.

Subjects
Organic compounds -- Synthesis, Acylation -- Research, Ring formation (Chemistry) -- Research, Stereochemistry -- Research, Biological sciences, Chemistry
Abstract

The dihydropyrone-based logic was used to secure the stereochemical elements of the epothilones. The initial step was a merger of the readily available enantiomerically homogeneous aldehyde with a diene, a stereochemically tunable version of the diene-aldehyde cyclocondensation reaction. A possible approach for macrocyclization was also identified in the acylation of alcohol to provide esters using two model ----unsaturated acids. The compounds underwent olefin metathesis macrocyclization in the desired manner.

Published
1996

5. Studies toward a synthesis of epothilone A: use of hydropyran templates for the management of acyclic stereochemical relationships

Author

Meng, Dongfang, Sorensen, Erik J., Bertinato, Peter, and Danishefsky, Samuel J.

Subjects
Organic compounds -- Synthesis, Stereochemistry -- Research, Biological sciences, Chemistry
Abstract

The power of hydropyran matrices in addressing problems associated with the management of stereochemistry in acyclic intermediates was illustrated in the identification of a compound as a synthetic intermediate. Two routes were used for the synthesis of the compound. The first proceeds with the known aldehyde and involves such processes as homologation, cyclocondensation, Luche reduction, mesylation, deprotection and cyclization. The other route involves cyclocondensation and Emmons condensation.

Published
1996

7. In vitro and in vivo profile of 5-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid benzylmethyl carbamoylamide (dirlotapide), a novel potent MTP inhibitor for obesity

Author

Li, Jin, primary, Bronk, Brian S., additional, Dirlam, John P., additional, Blize, Alan E., additional, Bertinato, Peter, additional, Jaynes, Burton H., additional, Hickman, Anne, additional, Miskell, Christine, additional, Pillai, Usha A., additional, Tibbitts, Jay S., additional, Haven, Michelle L., additional, Kolosko, Nicole L., additional, Barry, Chris J., additional, and Manion, Tara B., additional

Published
2007
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9. Azalide 3,6-Ketals: antibacterial activity and structure–Activity relationships of aryl and hetero aryl substituted analogues

Author

Sakya, Subas M, primary, Bertinato, Peter, additional, Pratt, Bryan, additional, Suarez-Contreras, Melani, additional, Lundy, Kristin M, additional, Minich, Martha L, additional, Cheng, Hengmiao, additional, Ziegler, Carl B, additional, Kamicker, Barbara J, additional, Hayashi, Shigeru F, additional, Santoro, Sheryl L, additional, George, David M, additional, and Bertsche, Camilla D, additional

Published
2003
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12. Stereoselective syntheses and evaluation of compounds in the 8-desmethylepothilone A series: Some surprising observations regarding their chemical and biological properties

Author

Balog, Aaron, primary, Bertinato, Peter, additional, Su, Dai-Shi, additional, Meng, Dongfang, additional, Sorensen, Erik, additional, Danishefsky, Samuel J., additional, Zheng, Yu-Huang, additional, Chou, Ting-Chao, additional, He, Lifeng, additional, and Horwitz, Susan B., additional

Published
1997
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15. Totalsynthese von (—)‐Epothilon A

Author

Balog, Aaron, primary, Meng, Dongfang, additional, Kamenecka, Ted, additional, Bertinato, Peter, additional, Su, Dai‐Shi, additional, Sorensen, Erik J., additional, and Danishefsky, Samuel J., additional

Published
1996
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16. Total Synthesis of(–)-Epothilone A

Author

Balog, Aaron, primary, Meng, Dongfang, additional, Kamenecka, Ted, additional, Bertinato, Peter, additional, Su, Dai-Shi, additional, Sorensen, Erik J., additional, and Danishefsky, Samuel J., additional

Published
1996
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18. Total Synthesis of Rapamycin

Author

Nicolaou, K. C., primary, Piscopio, Anthony D., additional, Bertinato, Peter, additional, Chakraborty, Tushar K., additional, Minowa, Nobuto, additional, and Koide, Kazunori, additional

Published
1995
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19. Synthesis and kinetics of decomposition of 7-(2-cyanoethyl)guanine and O-(2-cyanoethy)guanine, markers for reaction of acrylonitrile and 3-(methylnitrosamino)propionitrile with DNA.

Author

Prokopczyk, Bogdan, Bertinato, Peter, and Hoffmann, Dietrich

Abstract

Acrylonitrile, a carcinogen in rodents, is used in the large-scale production of acrylic polymers. 3-(Methylnitrosamino)propionitrile, a potent carcinogen in Fischer rats, is an Areca-derived nitrosamine which has been found in the saliva of betel quid chewers. Upon metabolic activation, both of these carcinogens can react with DNA to form 7-(2-cyanoethyl)guanine and -(2-cyanoethyl)guanine. The latter has never been described. We have therefore synthesized this derivative by reacting 2-(-carbethoxy--nitrosamino)propionitrile with deoxyguanosine. [ABSTRACT FROM PUBLISHER]

Published
1988

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