181300-46-9Relevant academic research and scientific papers
Synthesis of Cadinanolide Type of Tricyclic α-Methylene-γ-lactone Using Intramolecular Cyclization of α-Trimethylsilylmethyl-α,β-Unsaturated Ester with Cyclic Ketone
Kuroda, Chiaki,Ito, Kunihito
, p. 2297 - 2303 (1996)
Fluoride-promoted intramolecular cyclization of ethyl 6-(2-oxocyclohex-1-yl)-2-(trimethylsilylmethyl)hex-2-enoate afforded ethyl 2-(1-hydroxybicyclo[4.4.0]decan-2-yl)acrylate as the major product, together with tricyclic α-methylene-γ-lactone, a model compound of cadinanolides. The former product was also converted to γ-lactone. The cyclization reaction promoted by TiCl4 gave the hydroxy ester and its dehydrated product. Both Lewis acid- and fluoride-promoted cyclizations gave a trans-decaline system mainly. This stereoselectivity is completely different from that of Reformatsky cyclization observed by Dreiding and co-workers.
Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones
Morisson,Barnier,Blanco
, p. 7749 - 7764 (2007/10/03)
Optically active α-methyl α-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives.
