76375-87-6

Upstream product

• 80054-40-6 (2E,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial 
• 156155-54-3 (2E/Z,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial 
• 76338-09-5 (1R,2S,3R,3aR)-3,6-Dimethyl-1,2,3,3a,4,5-hexahydro-pentalene-1,2-diol 
• 76338-04-0 Acetic acid (1R,2S,3S,3aS,6S,6aS)-2-acetoxy-6-hydroxy-3,6-dimethyl-octahydro-pentalen-1-yl ester 
• 76338-04-0 Acetic acid (1S,2R,3S,3aS,6S,6aS)-2-acetoxy-6-hydroxy-3,6-dimethyl-octahydro-pentalen-1-yl ester 
• 76338-07-3 Acetic acid (1S,2R,3S,3aS)-2-acetoxy-3,6-dimethyl-1,2,3,3a,4,5-hexahydro-pentalen-1-yl ester 
• 83912-24-7 (S)-2-((R)-2-[1,3]Dioxolan-2-yl-3-methyl-cyclopent-2-enyl)-propionaldehyde 
• 73719-06-9 1,2-Dihydroxy-5-isopropenyl-2-methyl-cyclopentanecarboxylic acid methyl ester 
• 83912-22-5 (S)-2-((R)-2-[1,3]Dioxolan-2-yl-3-methyl-cyclopent-2-enyl)-propan-1-ol 
• 73719-05-8 methyl 3-isopropenyl-2,6-dioxoheptanoate 
• 83912-23-6 2-(5-Isopropenyl-2-methyl-cyclopent-1-enyl)-[1,3]dioxolane 
• 73136-32-0 methyl (+/-)-5-isopropenyl-2-methyl-1-cyclopentene-1-carboxylate 
• 3865-09-6 5-isopropenyl-2-methylcyclopent-1-ene carboxaldehyde 
• 60168-94-7 3-isopropenyl-1-methyl-2-hydroxymethyl-1-cyclopentene 

Downstream Products

• 21700-67-4 isodehydroiridodiol (3R^*,8R^*) 
• 550-45-8 dl-Iridodial 
• 21700-67-4 (+/-)-dehydroiridodiol 

Relevant academic research and scientific papers

FUNCTIONALIZED CYCLOPENTANE DERIVATIVES FROM THE PHOTOADDUCTS OF METHYL 2,4-DIOXOPENTANOATE-OLEFINS: ALTERNATIVE SYNTHESES OF dl-DEHYDROIRIDODIAL AND dl-CHRYSOMELIDIAL

Functionalized cyclopentane derivatives were prepared by the retro-ozonolysis of methyl 2,6-dioxoheptanoates, which are readily accessible from the photocycloaddition of methyl 2,4-dioxopentanoate with olefins.By this method, 3-isopropenyl-2-methoxycarbonyl-1-methylcyclopentene, a versatile intermediate to iridoid terpenoids, and 1-methoxycarbonyl-2,6,6-trimethylfulvene were synthesized from isoprene.Alternative syntheses of dl-dehydroiridodial and dl-chrysomelidial were accomplished.

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).

TRICYCLO2,8>OCTANONES AS BUILDING BLOCKS IN NATURAL PRODUCTS SYNTHESIS (I). --THE SYNTHESIS OF CHRYSOMELIDIAL--

The stereocontrolled synthesis of chrysomelidial from 4-methyl-tricyclo2,8>octan-3-one is described.