229645-36-7Relevant academic research and scientific papers
Synthesis of the tricyclic triamine core of martinelline and martinellic acid
Snider, Barry B.,Ahn, Yong,Foxman, Bruce M.
, p. 3339 - 3342 (1999)
The tricyclic triamine core 27 of martinellic acid (2) has been prepared stereospecifically in eight steps from 2-hydroxymethylaniline in 11% overall yield. The key steps are the addition of 2-hydroxymethylaniline to vinylcyclopropane 14 to prepare cycloaddition precursor 19 in only two steps and an intramolecular [3+2] azomethine ylide cycloaddition reaction to produce tetracycle 20 with >9:1 diastereoselectivity.
Total synthesis of (+/-)-martinellic acid.
Snider,Ahn,O'Hare
, p. 4217 - 4220 (2007/10/03)
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]
