Rhodium (II)-Catalyzed Decomposition of 1-Diazo-4-(1-or 2-naphthyl)-2-butanones as a New Route to Rearranged Pimarane and Abietane Skeleta. Synthesis of …

P Manitto, D Monti, G Speranza

文献索引：Manitto, Paolo; Monti, Diego; Zanzola, Simona; Speranza, Giovanna Journal of Organic Chemistry, 1997 , vol. 62, # 19 p. 6658 - 6665

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被引用次数: 19

摘要

The Rh2 (OAc) 4-catalyzed intramolecular Buchner reaction of 1-diazo-4-(1-or 2-naphthyl) butan-2-ones was examined as a potential route to abietane and rearranged abietane derivatives. Treatment of the α-diazo ketone 26 with catalytic amount of dirhodium tetraacetate in CH2Cl2 at 0° C furnished the tetracyclic derivative 27 in good yield. Addition of TFA to 27 (in CH2Cl2) resulted in an acid-induced opening of the cyclopropane ring to ...