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.
Keywords: Diels–Alder reactions; o-benzoquinones; cis-decalins; triquinanes; total synthesis.
*An issue of reviews and research papers based on lectures presented at the 15th International Conference on Organic Synthesis (ICOS-15), held in Nagoya, Japan, 1-6 August 2004, on the theme of organic synthesis. Other presentations are published in this issue, pp. 1087-1296.