Patent ID: 6482851
Filing Date: 2002-11-19
Classification: A61K,C07C,C07D,C07F

Abstract:
A process for the preparation of a racemic mixture of dysidiolide analogue of the formula: comprising the steps of:(a) adding lithium dimethylcuprate to a dioxolane; (b) trapping the compound formed in step (a) under suitable conditions to form an olefin; (c) converting the ester function to a protected two carbon alcohol residue to form a dienophile; (d) converting a ketone, derived by alkylating with an alkyl iodide, to vinyl triflate; (e) performing a Stille cross coupling on the vinyl triflate of (d) under suitable conditions to form a diene; (f) performing a Diels Alder reaction on the dienophile of step (c) and the diene of step (e) under suitable conditions to form a compound having the structure: (g) cleaving the acetal function of the compound in (f) under suitable conditions to form a compound having the structure: (h) performing a Wolff Kishner reduction and desilylating the compound in step (g) to form an alcohol having the structure: (i) oxidizing the alcohol formed in step (h) under suitable conditions to form an aldehyde; (j) treating the aldehyde in step (i) with 3-lithiofuran and photo-oxidizing under suitable conditions to form a racemic mixture of dysidiolide.