615577-70-3

Upstream product

• 615577-68-9 (1S,3R,4aR,5R,8aS)-4a-hydroxy-3-isopropenyl-5,8a-dimethyl-1,2,3,4,4a,5,8,8a-octahydro-1-naphthalenyl benzoate 
• 615577-55-4 (1R,2S,3R,5R)-2-allyl-5-isopropenyl-2-methyl-1-[(1R)-1-methyl-2-propenyl] cyclohexane-1,3-diol 
• 615577-67-8 (1S,3R,4aR,5R,8aS)-3-isopropenyl-5,8a-dimethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4a-naphthalenediol 
• 615577-57-6 (1R,3R,4aR,5R,8aS)-3-isopropenyl-5,8a-dimethyl-1,2,3,4,4a,5,8,8a-octahydro-1,4a-naphthalenediol 
• 615577-66-7 (3S,4aR,5R,8aR)-4a-hydroxy-3-isopropenyl-5,8a-dimethyl-1,2,3,4,4a,5,8,8a-octahydro-1-naphthalenone 
• 615577-52-1 (2S,3R,5R)-2-allyl-3-hydroxy-5-isopropenyl-2-methylcyclohexan-1-one 
• 615577-69-0 (1S,3R,5R,8aR)-3-isopropenyl-5,8a-dimethyl-1,2,3,5,8,8a-hexahydro-1-naphthalenyl benzoate 
• 6485-40-1 (R)-Carvone 
• 36616-60-1 (1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one 

Downstream Products

• 615577-71-4 (3aS,4aR,5S,7R,9S,9aR)-7-(1-hydroxy-1-methylethyl)-2,2,4a,9-tetramethyl-3a,4,4a,5,6,7,9,9a-octahydronaphtho[2,3-d][1,3]dioxol-5-yl benzoate 
• 615577-72-5 (1aS,2R,4S,4aS,5aS,8aR,9R,9aR)-2-(1-hydroxy-1-methylethyl)-4a,7,7,9-tetramethylperhydrooxireno[2',3':4a,5]naphtho[2,3-d][1,3]dioxol-4-yl benzoate 

Relevant academic research and scientific papers

A versatile, RCM based approach to eudesmane and dihydroagarofuran sesquiterpenoids from (-)-carvone: A formal synthesis of (-)-isocelorbicol

An enantiospecific and diversity oriented approach to a range of functionalized eudesmane, nor-, iso-, and dihydroagarofuran frameworks from (-)-carvone is delineated. The cornerstone of this approach is the installation of the quaternary carbon center through reductive opening of the carvone epoxide and setting-up of RCM reaction to generate the bicyclic eudesmane framework. Various options like carbocation mediated oxycyclization and intramolecular hydroxy directed epoxide opening have been explored for the construction of the bridged tetrahydrofuran moiety. Among the several eudesmane and dihydroagarofurans accessed during the present study, one has been previously elaborated to isocelorbicol, thus constituting its formal synthesis.

A general, ring closure metathesis based enantiospecific approach to polyfunctional eudesmane, eremophilane and agarofuran sesquiterpenoids

An enantiospecific and stereo- and functional group diversity oriented approach to eudesmane, eremophilane and agarofuran sesquiterpenoids from (-)-carvone has been devised. RCM has been employed as the key reaction to generate the highly functionalized eudesmane framework. Further elaboration of the eudesmane framework to agarofurans and biogenetic-type rearrangement to eremophilanes is outlined.