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Total synthesis of (+/-)-martinellic acid.

A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH(4) and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degrees C as key steps. [structure: see text][1]

References

  1. Total synthesis of (+/-)-martinellic acid. Snider, B.B., Ahn, Y., O'Hare, S.M. Org. Lett. (2001) [Pubmed]
 
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