J. Reuvers, J. Wijnberg, A. de Groot
Sep 2, 2010
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Recueil des Travaux Chimiques des Pays-Bas
Abstract
A synthesis of 3β-acetoxy-2aα,5aβ-dimethyl-3,4,5,5a,7,8,8aα,8bα-octahydro-2H-naphtho-[1,8-bc]furan-2,6(2aH)-dione 1 is explored starting from 5β-acetoxy-1,4aβ-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 2 and methyl 5,5-(ethylenedioxy)-2-oxo-4aβ-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carboxylate 3. A successful route to lactone 1 was found via methylation and reduction of oxo ester 3 to methyl 5-oxo-2β-acetoxy-1α,4aβ-dimethyl-1,2,3,4,4a,5,6,7,8,8aα-decahydronaphthalene-1β-carboxylate 5. Transformation of 5 into 5-oxo-2β-acetoxy-6-bromo-1α,4aβ-dimethyl-1,2,3,4,4a,5,8,8aα-octahydronaphthalene-1β-carboxylic acid 13, followed by lactonization and reduction, gave lactone 1.