Total synthesis of (+/-)-symbioimine.
The synthesis of (+/-)-symbioimine (1) has been completed in only 12 linear steps in 8% overall yield. The key step is the treatment of 13b with BF3.Et2O to generate N-carboalkoxydihydropyridinium cation 14b, which undergoes a novel stereospecific intramolecular Diels-Alder reaction to give adduct 16b in 42% yield. Cleavage of the N-Troc group of 16b afforded imine 24b stereospecifically. Cleavage of the TBDMS ethers and sulfation provided (+/-)-symbioimine (1). [reaction: see text].
Zou
Yefen
Y
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Che
Qinglin
Q
Snider
Barry B
BB
D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010100:Oxygen / Q000737:chemistry; D010753:Phosphoranes / Q000737:chemistry; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry
D006575:Heterocyclic Compounds, 3-Ring; D007202:Indicators and Reagents; D010753:Phosphoranes; D013431:Sulfates; C505668:symbioimine; D010100:Oxygen