89396-47-4

Upstream product

• 1074-86-8 4-formyl indole 
• 16136-52-0 4-cyanoindole 
• 76084-18-9 t-butyl trans-N(5-formyl-1,3,4,5-tetrahydrobenzindol-4-yl)N-methylcarbamate 
• 76084-18-9 t-butyl cis-N(5-formyl-1,3,4,5-tetrahydrobenzindol-4-yl)N-methylcarbamate 
• 76084-17-8 t-butyl-N-<(4R^*,5S^*,1'S^*)-5-(1',2'-dihydroxyethyl)-1,3,4,5-tetrahydrobenzindol-4-yl>N-methylcarbamate 
• 76084-14-5 methyl(6aR^*,9S^*,9aS^*)-4,6,6a,7,9,9a-hexahydro-7-methylindolo<4,3 - e,f><2,1>benzisoxazole-9-carboxylate 
• 89368-47-8 methyl 5-methyl-4,7-methano-3H-<1,3>oxacino<5,6,7 - cd>indole-11-carboxylate 
• 76084-15-6 ((6aR,9S,9aS)-7-Methyl-4,6,6a,7,9,9a-hexahydro-8-oxa-4,7-diaza-cyclopenta[e]acenaphthylen-9-yl)-methanol 
• 76084-21-4 (E)-methyl-3-(3-cyanomethyl-4-indolyl)propenoate 
• 76084-22-5 (E)-3-[3-(2-Oxo-ethyl)-1H-indol-4-yl]-acrylic acid methyl ester 
• 74059-91-9 3-(N,N-dimethylaminomethyl)-4-indolecarbaldehyde 
• 76084-20-3 (E)-methyl 3-(1H-indol-4-yl)acrylate 
• 89368-50-3 3-cyanomethylindole-4-carbaldehyde 
• 89368-45-6 t-butyl(4R^*,5S^*,1'R^*)-N-<5-(2'-methyl-2'-propen-1'-ol)-1,3,4,5-tetrahydrobenzindolyl>N-methylcarbamate 

Relevant academic research and scientific papers

TOTAL SYNTHESES OF CLAVINE ALKALOIDS BY AN INTRAMOLECULAR NITRONE-OLEFIN CYCLOADDITION REACTION

The racemic ergot alkaloids chanoclavine I (1) and 6,7-secoagroclavine (4) have been synthesized stereoselectively from indole-4-carboxaldehyde (7) in overall yields of 14 and 13 percent, respectively.Further syntheses of isochanoclavine I (2), paliclavine (5) and costaclavine (6), via the same isoxazolidine 18 are described.The key step 16-->18 (Scheme 4) involves a transient nitrone 17 which undergoes a kinetically controlled, regio- and stereoselective intramolecular cycloaddition to a 1,2-disubstituted olefinic bond.