A practical and efficient preparation of (−)-(4aS, 5R)-4, 4a, 5, 6, 7, 8-hexahydro-4a, 5-dimethyl-2 (3H)-naphthalenone: a key intermediate in the synthesis of (−)- …

…, PRR Costa, I Caracelli, J Zukerman-Schpector

Index: Schenato, Rossana A.; Dos Santos, Everton M.; Tenius, Beatriz S.M.; Costa, Paulo R.R.; Caracelli, Ignez; Zukerman-Schpector, Julio Tetrahedron Asymmetry, 2001 , vol. 12, # 4 p. 579 - 584

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Citation Number: 18

Abstract

A novel diastereoselective route to octalone (−)-1 has been developed. The key step involves an asymmetric Michael addition of the corresponding chiral secondary enamines derived from (S)-(−)-1-phenylethylamine and (3R)-2, 3-dimethylcyclohexanone to methyl vinyl ketone. This enone was successfully transformed into the eremophilane-type sesquiterpenoid (−)-dehydrofukinone.