21700-67-4

Upstream product

• 77116-74-6 (E)-2-hexenedioic acid diethyl ester 
• 29311-53-3 (E)-3-hexene-1,6-dioic acid 
• 107932-86-5 2-(1-tert-Butoxycarbonyl-ethyl)-5-oxo-cyclopentanecarboxylic acid ethyl ester 
• 63808-11-7 dl-chrysomelidial 
• 107932-88-7 (R)-5-((R)-1-tert-Butoxycarbonyl-ethyl)-2-methyl-cyclopent-1-enecarboxylic acid ethyl ester 
• 107711-63-7 2-methyl-5-(1-methyl-2-tetrahydropyranyloxy) ethylcyclopentene-1-carboaldehyde 
• 125002-54-2 tetrahydropyranyl ether of (E)-7-hydroxy-6-methyl-5-hepten-2-one 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 85447-92-3 (4S,4aR)-4,7-Dimethyl-1,3,4,4a,5,6-hexahydro-cyclopenta[c]pyran-3-ol 
• 107932-88-7 (R)-5-((S)-1-tert-Butoxycarbonyl-ethyl)-2-methyl-cyclopent-1-enecarboxylic acid ethyl ester 
• 63808-11-7 dl-dehydroiridodial 
• 80054-40-6 (2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial 
• 125002-55-3 (E)-3,7-Dimethyl-8-(tetrahydro-pyran-2-yloxy)-oct-6-en-1-yn-3-ol 
• 71846-54-3 (E)-7-hydroxy-6-methylhept-5-en-2-one 

Relevant academic research and scientific papers

STEREOSELECTIVE TOTAL SYNTHESES OF (+/-)- AND OPTICALLY ACTIVE DEHYDROIRIDODIOLS

(+/-)-Dehydroiridodiol and its epimer (+/-)-isodehydroiridodiol were synthesized stereoselectively using the homoconjugate addition of cyanide anion to methyl 6-methyl-2-oxobicyclohexane-1-carboxylates.Both enantiomers of dehydroiridodiol were prepared after the resolution of l-menthyl 6-methyl-2-oxobicyclohexane-1-carboxylate, whose absolute configurations became clear as the result.

A DIASTEREO- AND ENANTIOSELECTIVE MICHAEL ADDITION OF CHIRAL AMIDE ENOLATES TO α,β-UNSATURATED ESTERS; A STEREOSELECTIVE SYNTHESIS OF (+)-DEHYDROIRIDODIOL AND (-)-ISODEHYDROIRIDODIOL

(+)-Dehydroiridodiol and (-)-isodehydroiridodiol were synthesized stereoselecticely using the diastereo- and enantioselective Michael addition of chiral amide enolates to α,β-unsaturated esters.

THE BASE-CATALYZED CYCLIZATION OF 10-OXOCITRAL. SYNTHESIS OF CHRYSOMELIDIAL AND DEHYDROIRIDODIAL

Base treatment of 10-oxocitral (1) gives chrysomelidial (9) and dehydroiridodial (10), supporting the intermediacy of 1 in the biosynthesis of some iridoid glucosides.Cannizzaro reaction of 9 and 10 affords regioselectively a new iridolactone, 1,2-dehydroisoiridomirmecin (13).