Regioselective Lewis Acid-Directed Reactions of 2-Alkoxy-5-alkyl-1,4-benzoquinones with Styrenes: Synthesis of Burchellin and Guianin Neolignans

• Published in: Journal of organic chemistry Vol. 59; no. 22; pp. 6588 - 6599
• Main Authors: Engler, Thomas A, Wei, Dong Donna, Letavic, Michael A, Combrink, Keith D, Reddy, Jayachandra P
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.11.1994; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; TITANIUM TETRACHLORIDE; ALKENES; DIELS-ALDER REACTIONS; QUINONES; CRYSTAL-STRUCTURE; SIMULTANEOUS COORDINATION; ALDEHYDE COMPLEXES; ADDITIONS; C-13 NMR-SPECTROSCOPY; DERIVATIVES

Reactions of 2-carbomethoxy-5-methoxy-1,4-benzoquinone with (E)-propenylbenzenes promoted by Ti(IV) regio- and stereoselectively yield trans 2-aryl-4-carbomethoxy-7-methoxy-3-methyl-2,3-dihydro-5-benzofuranols. However, the products found in Lewis acid-promoted reactions of 2-alkoxy-5-alkyl-1,4-benz...