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Total synthesis of diaeudesmin and epieudesmin enantiomers from diallyl

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Abstract

A total synthesis of both pairs of enantiomers of natural lignans, diaeudesmin and epieudesmin, was described. The synthesis involved enantioselective allylborylation of veratraldehyde with 1,6-bis(diisopinocampheylboryl)hexa-2,4-dienes, ozonolysis, and triethylsilane reduction in the presence of boron trifluoride etherate.

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Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. E. Gursky, S. V. Baranin & Yu. N. Bubnov

  2. Department of Chemistry, Lomonosov Moscow State University, 3 Build., 1 Leninskie Gory, 119991, Moscow, Russian Federation

    K. A. Lyssenko

  3. Plekhanov Russian University of Economics, 36 Stremyannyi per., 117997, Moscow, Russian Federation

    K. A. Lyssenko

  4. Institute of Fundamental Problems of Biology, Russian Academy of Sciences, 2 ul. Institutskaya, 142290, Pushchino, Moscow Region, Russian Federation

    O. O. Chudakova

Authors
  1. M. E. Gursky
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  2. S. V. Baranin
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  3. K. A. Lyssenko
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  4. O. O. Chudakova
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  5. Yu. N. Bubnov
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Corresponding author

Correspondence to S. V. Baranin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. A. Tartakovsky on the occasion of his 90th birthday.

The authors are grateful to Academician of the Russian Academy of Science V. P. Ananikov and PhD N. V. Orlov (both from N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences) for determination of enantiomeric purity of the synthesized diols (−)-5 and (+)-5 using the procedure developed by them earlier.38

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1729–1736, August, 2022.

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Gursky, M.E., Baranin, S.V., Lyssenko, K.A. et al. Total synthesis of diaeudesmin and epieudesmin enantiomers from diallyl. Russ Chem Bull 71, 1729–1736 (2022). https://doi.org/10.1007/s11172-022-3583-2

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  • DOI: https://doi.org/10.1007/s11172-022-3583-2

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