1997 cycloaddition reactions

cycloaddition reactionsO 0070

43 - 050Novel Methodology for Stereocontrolled Synthesis of cis-Decalins.— Highly functionalized cis-decalins (cf. (IV), 6 examples) are synthesizedvia endo-selective cycloaddition reactions of commercially available catecholderivatives with trans-dienols. The tricyclic side products (III) undergo Coperearrangements to the desired decalins on heating in mesitylene. When cis-pentadienol (V) is employed as a dienol, only the tricyclic compounds (cf. (VI))are obtained. — (HSIU, P.-Y.; LIAO, C.-C.; Chem. Commun. (Cambridge)(1997) 12, 1085-1086; Dep. Chem., Natl. Tsing Hua Univ., Hsinchu 30043,Taiwan; EN)

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