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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Structure Reassignment and Synthesis of Jenamidines A(1)/A(2), Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues.

The proposed structures of jenamidines A, B, and C (1-3) were revised to jenamidines A(1)/A(2), B(1)/B(2), and C (8-10). Jenamidines A(1)/A(2) (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.[1]

References

  1. Structure Reassignment and Synthesis of Jenamidines A(1)/A(2), Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues. Duvall, J.R., Wu, F., Snider, B.B. J. Org. Chem. (2006) [Pubmed]
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