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Pure Appl. Chem., 2005, Vol. 77, No. 7, pp. 1221-1234

Masked o-benzoquinone strategy in organic synthesis: Short and efficient construction of cis-decalins and linear triquinanes from 2‑methoxyphenols

Chun-Chen Liao

Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan

Abstract: The inter- and intramolecular Diels–Alder reactions of masked o-benzoquinones generated in situ from the oxidation of easily accessible 2-methoxyphenols with diacetoxyiodobenzene or bis(trifluoroacetoxy)iodobenzene provided cycloadducts in excellent regio- and stereoselectivity and good yields. A general approach to the synthesis of highly substituted cis-decalins and triquinanes with complete stereocontrol from the cycloadducts has been developed. The applicability of our methodology is demonstrated by the total syntheses of several natural products.