Abstract
The tricyclic triamine core27 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 vinylcyclopropane14 to prepare cycloaddition precursor19 in only two steps and an intramolecular [3+2] azomethine ylide cycloaddition reaction to produce tetracycle20 with>9:1 diastereoselectivity.