Synthesis of the putative active metabolites of the cyclopenta [a] phenanthrenes. Synthesis of the trans-3, 4-dihydro-3, 4-diol and syn-3, 4-diol 1, 2-epoxide derivatives …

SA Woski, M Koreeda

Index: Woski, Stephen A.; Koreeda, Masato Journal of Organic Chemistry, 1992 , vol. 57, # 21 p. 5736 - 5741

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Citation Number: 16

Abstract

The first synthesis of the trans-dihydro diol and syn-diol epoxide derivatives of a biologically active cyclopenta [a] phenanthrene is described. The cyclopenta [a] phenanthrene skeleton is rapidly and efficiently assembled utilizing the Lewis acid-catalyzed Diels-Alder reaction of 1, 2-dihydr0-7-methoxy-4-vinylnaphthalene (5) with an a-heterosubatituted cyclopentenone, a'cyclopentynone" equivalent. It was found that the Dieh-Alder reaction of a-( ...