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Synthesis of 3a,6,6,9a-tetramethyl-trans-perhydronaphtho [2,1-b]furan and 4a,7,7,10a-tetramethyl-trans-perhydronaphtho [2,1-b]pyran

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The compounds 3a,6,6,9a-tetramethyl-trans-perhydronaphtho[2,1-b]furan (ambrox or ambroxide) and 4a,7,7,10a-tetramethyl-trans-perhydronaphtho[2,1-b]pyran (homofixator) — substances important in the perfume industry — have been synthesized by superacid cyclization of E,E-homofarnesol and E,E-bishomofarnesol or mixtures of the isomeric bicyclohomofarnesenes or bicyclobishomofarnesenols. Superacid cyclization of these alcohols was shown to be an effective structurally selective and stereospecific method of obtaining ambroxide and homofixator.

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Authors and Affiliations

  1. Institute of Chemistry, Academy of Sciences of the Moldavian SSR, 277028, Kishinev

    P. F. Vlad, N. D. Ungur & V. B. Perutskii

Authors
  1. P. F. Vlad
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  2. N. D. Ungur
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  3. V. B. Perutskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 896–901, July, 1990.

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Vlad, P.F., Ungur, N.D. & Perutskii, V.B. Synthesis of 3a,6,6,9a-tetramethyl-trans-perhydronaphtho [2,1-b]furan and 4a,7,7,10a-tetramethyl-trans-perhydronaphtho [2,1-b]pyran. Chem Heterocycl Compd 26, 746–750 (1990). https://doi.org/10.1007/BF00509700

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  • DOI: https://doi.org/10.1007/BF00509700

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