Efficient synthesis of fused bicyclic glutarimides. Its application to (+/-)-alloyohimbane and louisianin D.
[reaction: see text] The reaction of alpha-sulfonyl acetamide 1 with various cyclic unsaturated esters 2 to fused bicyclic glutarimides is reported. Syntheses of (+/-)-alloyohimbane (4) and louisianin D (5) have been accomplished.
Chen
Hung-Wei
HW
Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan.
Hsu
Ru-Ting
RT
Chang
Meng-Yang
MY
Chang
Nein-Chen
NC
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D004952:Esters; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000498:Allyl Compounds; D004952:Esters; D006576:Heterocyclic Compounds, 4 or More Rings; D010881:Piperidones; D011725:Pyridines; C518945:alloyohimbane; C096933:louisianin D; C007864:glutarimide