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Cyclization of isoprenoid compounds Communication 11. Cyclization of isomeric farnesylic esters and their monocyclic analogs

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The cyclization of cis-(6,7)- and trans-(6,7)-farnesylic esters into bicyclo products goes kinetically in two stages. Under mild conditions reaction can be stopped at the first stage, and from the cis-(6, 7) isomerα-monocyclofarnesylic ester is formed, whereas from the trans-(6,7) isomer (β-monocyclofarnesylic ester is formed.

  2. 2.

    Irrespective of the cis-trans configuration of the 6,7-double bond of the farnesylic ester, and also of the position of the double bond (α orβ) in its monocyclic analogs, bicyclofamesylic esters of the trans-decalin series are formed exclusively, i. e., the formation of the decalin system goes nonstereospecifically.

  3. 3.

    Addition at the conjugated 10, 11-double bond in the second stage of the reaction goes, as in the case of apofarnesylic acids, stereospecifically with formation of epimericα-bicyclofarnesylic esters, i. e., the stereospecificity of addition at this bond is not related to the degree to which it is substituted.

  4. 4.

    A mechanism scheme is proposed for the process, and the prerequisites for the stereospecific formation of the carbobicyclic system are discussed.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences, USSR

    A. V. Semenovskii, V. A. Smit & V. F. Kucherov

Authors
  1. A. V. Semenovskii
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  2. V. A. Smit
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  3. V. F. Kucherov
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Translated from Izvestiya Akadeemii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1424–1433, August, 1965 Original article submitted June 14, 1963

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Semenovskii, A.V., Smit, V.A. & Kucherov, V.F. Cyclization of isoprenoid compounds Communication 11. Cyclization of isomeric farnesylic esters and their monocyclic analogs. Russ Chem Bull 14, 1383–1390 (1965). https://doi.org/10.1007/BF00846197

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  • DOI: https://doi.org/10.1007/BF00846197

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