Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues.

Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues. Research Abstract Details 

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Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues. Abstract Text:

Jeremy R Duvall,Fanghui Wu,Barry B Snider,

The proposed structures of jenamidines A, B, and C (1-3) were revised to jenamidines A1/A2, B1/B2, and C (8-10). Jenamidines A1/A2 (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA (76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues. Publishing Authors By Initials

JR Duvall,F Wu,BB Snider,

For similar heterocyclic compounds: alkaloids: pyrrolizidine alkaloids research abstracts see: heterocyclic compounds: alkaloids: pyrrolizidine alkaloids research

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Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: The Journal of organic chemistry

VOLUME: 71

Page Numbers: 8579-90

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 27

MONTH: Oct

YEAR: 2006

Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues. Keywords Mesh Terms:

KEYWORDS: Pyrrolizidine Alkaloids

MESH TERMS: chemistry

Chemical & Substance for Abstract: Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues. Information

Substance Name: Proline

Registry Number: 147-85-3

Grant and Affiliation Information for Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues.

AFFILIATION: Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM50151

ACRONYM: GM

MEDLINETA: J Org Chem

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