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

✍ Scribed by Raju Karmakar; Pallab Pahari; Dipakranjan Mal

Book ID
104096556
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
269 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 (e.g., 8) is also reported.

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