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Synthesis 1999; 1999(5): 854-858
DOI: 10.1055/s-1999-3483
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Synthesis of Several 8-Halopentacyclo[6.4.0.02,10.03,7.04,9]dodecane Derivatives

Pelayo Camps* , Xavier Pujol, Roberto A. Rossi, Santiago Vázquez
  • *Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal s/n; E-08028 Barcelona, Spain; Fax +3 49 34 03 59 41; E-mail: camps@farmacia.far.ub.es
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Publication Date:
31 December 1999 (online)

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The synthesis of pentacyclo[6.4.0.02,10.03,7.04,9]dodecane-8-carboxylic acid (7) from the known pentacyclo[6.4.0.02,10.03,7.04,9]dodecane-8,9-dicarboxylic acid (2) and its halodecarboxylation to the 8-bromo- (6), 8-chloro- (11) and 8-iodo- (10) derivatives is described. Hydrolysis of the methyl ester of 7 (5) with conc. sulfuric acid at around 90 °C gives the rearrangement product, 8-hydroxypentacyclo[6.5.0.02,11.03,7.04,10]tridecan-9-one (8).

8-chloro-(or 8-bromo or 8-iodo)pentacyclo [6.4.0.02,10.03,7.04,9]dodecane - 8-hydroxypentacyclo[6.5.0.02,11.03,7.04,10]tridecan-9-one - iodosobenzene diacetate - halodecarboxylation - rearrangement

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