13567-46-9

Upstream product

• 13567-40-3 5-cedranone 
• 469-61-4 α-Cedrene 
• 87017-57-0 9-hydroxy-2,8-dimethyltricyclo<5.3.1.0^1,5>undecane-6-spiro-1'-cyclopropane 
• 87017-57-0 C₁₅H₂₄O 

Downstream Products

• 13567-40-3 5-cedranone 
• 469-61-4 (+/-)-2-epi-methyl-α-cedrene 
• 469-61-4 (+/-)-cedrene 

Relevant academic research and scientific papers

A NEW SYNTHESIS OF (+/-)-CEDRENE USING SEQUENTIAL INTER- AND INTRA-MOLECULAR MICHAEL REACTIONS

A synthesis of (+/-)-cedrene (1), which features sequential intermolecular i.e.(2) -> (7), and intramolecular i.e. (8) -> (9), Michael reactions using the bicyclooctenone (2) as key intermediate, is described.

Bicyclooctenones in Synthesis. A New Synthesis of (+/-)-Cedrene using Sequential Inter- and Intra-molecular Michael Reactions

A new synthetic approach to cedrene (1) based on sequential inter- and intra-molecular Michael reactions using the bicyclooctenone (21) as the key intermediate is described.Michael addition of the enolate derived from (21) to 2-nitrobut-2-ene, led to a mixture of diastereoisomers of the nitro ketone (22), which was then converted into the 1,4-dione (23).Treatment of (23) with potassium t-butoxide in t-butyl alcohol resulted in smooth intramolecular Michael reaction leading to a mixture of α- (24a; major) and β-isomers of the tricyclo1,5>undecanedione (24) in a combined yield of 73percent.The undecanedione (24) was then converted into (+/-)-cedrene (1) and the corresponding methyl epimer (31a) via the intermediates (25), (26), (27), and (28).