Synthesis of Cadinanolide Type of Tricyclic <i>α</i>-Methylene-<i>γ</i>-lactone Using Intramolecular Cyclization of <i>α</i>-Trimethylsilylmethyl-<i>α</i>,<i>β</i>-Unsaturated Ester with Cyclic Ketone

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  • Synthesis of Cadinanolide Type of Tricyclic .ALPHA.-Methylene-.GAMMA.-lactone Using Intramolecular Cyclization of .ALPHA.-Trimethylsilylmethyl-.ALPHA.,.BETA.-Unsaturated Ester with Cyclic Ketone.
  • ChemInform Abstract: Synthesis of Cadinanolide Type of Tricyclic α‐Methylene‐γ‐ lactone Using Intramolecular Cyclization of α‐ Trimethylsilylmethyl‐α,β‐Unsaturated Ester with Cyclic Ketone.

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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.

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