Tetrahedron Letters

A synthetic route to 1, 3-dihydroisobenzofuran natural products: the synthesis of methyl ethers of pestacin

R Karmakar, P Pahari, D Mal

Index: Karmakar, Raju; Pahari, Pallab; Mal, Dipakranjan Tetrahedron Letters, 2009 , vol. 50, # 28 p. 4042 - 4045

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Citation Number: 10

Abstract

A synthetic route to 1-(2, 6-dihydroxyphenyl) phthalan natural products is described. It is typified by the synthesis of permethyl and monomethyl ethers (21 and 22) of pestacin (1), a 1, 3-dihydroisobenzofuran natural product. The key step is hydrodeoxygenation of the corresponding isobenzofuranone 19 in 2 steps: reduction and intramolecular etherification. A route involving hydrodesulfurization of a thionophthalide to a phthalan (eg, 8) is also ...