Tetrahedron Letters p. 3339 - 3342 (1999)
Update date:2022-08-02
Topics: Synthesis Catalyst Solvent Chromatography Extraction Reactant
Snider, Barry B.
Ahn, Yong
Foxman, Bruce M.
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.
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Doi:10.1021/acs.jmedchem.8b01413
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