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 ...
