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- Tetracyclic compound 5, is derived from the cyclobutane ring opening of pentacyclic ketone 4. the sequence of events leading to compound 5, was not investigated
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- Two modifications were made in the Haworth's synthesis: i) the reduction of the ketocarbonyl function of the 4-naphthalen-2-yl-4-oxo-butyric acid gave better results when Wolff-Kishner reaction was used instead of Clemmensen methodology;ii) the ring closure of the 4-naphthalen-2-yl-butyric acid to afford phenanthrenone 9, was accomplished using a more diluted aqueous H2SO4 solution. Under these conditions the reaction gave the yield reported by Haworth but it was reproducibile
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- the numbering system depicted in the formula of compounds 4, and 5, was based on an arbitrary choice
- the letters A and B are used to distinguish the sterically different hydrogens of the methylene group
- For general experimental details see ref [3]. All NMR spectra in CDCI3 (except for compounds 14, and 15, were run at room temperature (internal Me4Si) on a Varian Associates VXR-400 multinuclear instrument. Commercially available 1 M Hexane solution of ethylaluminumdichloride was used; methylene chloride was distilled from CaH2.-All Compounds gave a correct elemental analysis
- Based, in part, on the doctoral dissertations of Cristiano Casucci and Monia Velloni. c) Starred signals for compounds 2, 4–6, and 11–15, may be interchanged
- Aben , R. W. M. , Minuti , L. , Schewen , H. W. and Taticchi , A. 1991 . Tetrahedron Lett. , 32 : 6445
- Buchta , E. and Maar , H. 1964 . Liebigs Ann. Chem. , 674 : 129