Synthesis of Spiro[4.5]decan-1-ones: A Formal Synthesis of Acoradienes and Related Sesquiterpenes via Rhodium-catalyzed Claisen Rearrangement/Hydroacylation

Tim Sattelkau; Christoph Hollmann; Peter Eilbracht

doi:10.1055/s-1996-5707

Synlett 1996; 1996(12): 1221-1223
DOI: 10.1055/s-1996-5707

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Synthesis of Spiro[4.5]decan-1-ones: A Formal Synthesis of Acoradienes and Related Sesquiterpenes via Rhodium-catalyzed Claisen Rearrangement/Hydroacylation

Tim Sattelkau, Christoph Hollmann, Peter Eilbracht^*

^*Organische Chemie I (FB 3), Universität Dortmund, Otto-Hahn-Str. 6, D-44227 Dortmund, Germany, Fax: (+49) (0)231/7555363, e-mail: eilbrach@citrin.chemie.uni-dortmund.de

Abstract

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A novel procedure for the synthesis of spiro[4.5]decan-1-ones starting from commercially available substances is described. The key-step is a one-pot combination of Claisen rearrangement of allyl vinyl ethers followed by an intramolecular hydroacylation¹ catalysed by RhCl(cod)(dppe).² The intermediate pent-4-enals generated by the initial [3.3] sigmatropic rearrangement exhibit substitution patterns which have previously been described as unsuitable for the rhodium catalysed intramolecular hydroacylation.^3,4 This procedure allows the synthesis of ketone 2, a key intermediate in the total synthesis of acoradienes and acorones.⁵

acoradienes - spirocyclopentannulation - Claisen rearrangement - hydroacylation - transition metal catalysis

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