479681-33-9

Upstream product

• 479680-86-9 (1aR,2aS,6aR,7aR)-1a,2a,6,6-tetramethyl-octahydro-1-oxa-cyclopropa[b]naphthalen-2-one 
• 110188-61-9 (5S,6S)-6-(2-bromoallyl)-5-isopropenyl-2,6-dimethyl-2-cyclohexen-1-one 
• 138812-34-7 (R)-6-methylcarvone 
• 6485-40-1 (R)-Carvone 
• 4455-77-0 (methoxymethyl)diphenylphosphine oxide 

Relevant academic research and scientific papers

Synthetic studies on the preparation of oxygenated spongiane diterpenes from carvone

The paper describes a new diastereoselective approach to oxygenated spongiane diterpenes functionally related to natural dorisenones. The strategy followed for the preparation of the spongiane framework, a B→AB→ ABC→ABCD approach, is based on the preparation of epoxydecalone 11 (AB rings) from R-(-)-carvone, followed by an intramolecular Diels-Alder reaction for the construction of the C ring (compound 26). Further manipulation of the Diels-Alder adduct functionality allows the completion of the spongiane framework and the elaboration of several oxygenated spongiane-type compounds. The structures of two compounds 27 and 31, has been established by single-crystal X-ray crystallography.

Synthesis of oxygenated spongiane-type diterpenoids from carvone

A new diastereoselective approach to oxygenated spongiane diterpenes starting from (R)-(-)-carvone is described. The carvone is incorporated as the B ring in the final spongiane framework using a B→AB→ABC→ABCD approach, which involves an intramolecular Diels-Alder reaction and the regioselective ring-opening of a dihydrofuran ring as key synthetic steps. The structure of the key intermediate in this approach has been verified by X-ray crystallography.