Synthetic routes to benz [a] anthracenes via transient 1-benzylisobenzofuran derivatives

JG Smith, SS Welankiwar, NG Chu, EH Lai…

Index: Smith, James G.; Welankiwar, Sudha S.; Chu, Noreen G.; Lai, Eric H.; Sondheimer, Susan J. Journal of Organic Chemistry, 1981 , vol. 46, # 23 p. 4658 - 4662

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Citation Number: 7

Abstract

9 a, R= H; X= H b, R= Me; X= H c, R= H; X= OMe d, R= Me; X= OMe structural feature. The appropriate epoxytetrahydronaphthalenes, 4 were readily prepared by a Diels-Alder reaction of methyl acrylate with the transient isobenzofuran (Scheme 11). At this stage, the exo and endo isomers of 4 were separated and characterized. The stereochemistry of these compounds was established by the similarity of the characteristic patterns shown by the ...