Tetrahedron letters

Novel transformation of 2-substituted alkyl 1-indanone-2-acetates to 6-substituted 3, 4-benzotropolones through sequential reduction and oxidation processes using …

K Iwaya, M Tamura, M Nakamura, E Hasegawa

Index: Iwaya, Kazuki; Tamura, Mutsuko; Nakamura, Momoe; Hasegawa, Eietsu Tetrahedron Letters, 2003 , vol. 44, # 52 p. 9317 - 9320

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Citation Number: 18

Abstract

When 2-substituted alkyl 1-indanone-2-acetates 1 were treated with samarium diiodide, 3- substituted 2-hydroxy-2, 3-methano-1-oxo-1, 2, 3, 4-tetrahydronaphthalenes 4 were obtained. The reaction is proposed to proceed through a rearrangement initiated by intramolecular ketone–ester coupling. Oxidation of these products 4 or their silyl ethers 13 by ceric (IV) ammonium nitrate involving regioselective bond cleavage of their bicyclo [4.1. ...