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Simple synthesis of carvone using silyl enol ethers.

a simple synthesis of carvone using silyl enol ..

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Simple and convenient method ..

In 2007, we reported the development of a general method for the oxidative cross-coupling of 2-methyltetralone (39) to afford unsymmetrical 1,4-diketones (i.e., 42) with simultaneous generation of a quaternary stereocenter (). [] While modification of the tetralone component was somewhat limited, the reaction displayed good substrate scope for the methyl ketone component (representative examples shown), yielding 1,4-diketones in good yield. As had been a criterion from the outset, the synthesis of the unsymmetrical silyl bis-enol ethers could be conducted using only 1.1 equivalents of 40, negating the need for a large excess of one reacting partner.


There's been a lot of interest in these unusual looking natural products in the past decade with publications from Wood, Trost, Baran, Simpkins, Martin and Rawal all appearing in the literature. Credit for the first total synthesis of a member of this family goes to Rawal and coworkers, who reported a neat route to racemic N-methylwelwitindolinone D isonitrile back in March of this year, unfortunately before I'd started this blog.[1,2] This paper by Garg describes the first synthesis of N-methylwelwitindolinone C isothiocyanate to date, using a chiral pool based approach from (S)-carvone, and also contains lots of interesting chemistry.

18/04/2001 · The new triterpenoids of ..

Silyl enol ethers and ketene ..

Following these initial studies, we investigated the diastereoselective synthesis of linked bicyclic diketones using silyl bis-enol ethers. Initial studies focused on the dimerization of cyclohexanone via bis-enol ether 43 ().[]

A concise and simple synthesis of the ..

Selective catalytic conversion of pulegone in ..

The Journal of Supercritical Fluids" on DeepDyve, ..
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  • 1-Phenylthio-3-vinyl-3-cyclohexenol, a New Reagent …

    738 I

  • clear for the synthesis of simple ..

    Enol - Wikipedia

  • bicyclic diketones using silyl bis-enol ethers.

    The terms enol and alkenol are portmanteaus deriving from "-ene"/"alkene" and the ..

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