184719-44-6Relevant articles and documents
A synthetic entry to the trichothecene nucleus via cargill rearrangement. Formal synthesis of (±)-verrucarol
White, James D.,Kim, No-Soo,Hill, David E.,Thomas, James A.
, p. 619 - 626 (1998)
A formal synthesis of (±)-verrucarol (4) was completed via a route which began from 3-carbomethoxy-5-methyl-4-oxo-2H-pyran (22). A Diels-Alder reaction of this pyrone with 2-ethoxybuta-1,3-diene gave the bicyclic adduct 25, and a second annulation employing photoaddition of acetylene led to the cyclobutene 27. The latter underwent an acid-catalyzed Cargill rearrangement to lactone 28 which, after conversion to 34, suffered further rearrangement in the presence of a palladium(0) catalyst to 35. This tetracyclic lactone has previously been converted to (±)-verrucarol by Trost.