Journal of the Chemical Society. Perkin transactions I p. 811 - 817 (1984)
Update date:2022-07-30
Topics:
Horton, Michael
Pattenden, Gerald
A new synthetic approach to cedrene (1) based on sequential inter- and intra-molecular Michael reactions using the bicyclo<3.3.0>octenone (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 tricyclo<5.3.1.01,5>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).
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