A short synthesis of dimethyl tricyclo[3.3.0.03,7]octane‐1,5‐dicarboxylate and its 3,7‐dimethyl derivative. A new route to the tricyclo[3.3.0.03,7]octane skeleton

Pelayo Camps, Carmen Iglesias, María Jesús Rodríguez, María Desamparados Grancha, María Eugenia Gregori, Roberto Lozano, Miguel Angel Miranda, Marta Figueredo, Ana Linares

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18 Citations (Scopus)

Abstract

Five‐step syntheses of dimethyl tricyclo[3.3.0.03,7]octane‐1,5‐dicarboxylate (13) and its 3,7‐dimethyl derivative 14 from the readily available cis‐bicyclo[3.3.0]octane‐3,7‐diones 1 and 2, respectively, are described. The key‐step implies the iodine oxidation of the bis‐enolate derived from the corresponding dimethyl cis‐bicyclo‐[3.3.0]octane‐3,7‐dicarboxylates 11 and 12, thus being developed a new synthetic entry into the tricyclo[3.3.0.03,7]octane skeleton. Also, some attempts to synthesize diester 13 by using known methodology for the synthesis of compounds containing this tricyclic skeleton are described. Copyright © 1988 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Original languageEnglish
Pages (from-to)647-654
JournalChemische Berichte
Volume121
Issue number4
DOIs
Publication statusPublished - 1 Jan 1988

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