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Synthesis of phosphodiesterase IVb inhibitors 2. Stereoselective synthesis of hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one and tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one derivatives

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Abstract

The total stereoselective synthesis of two highly potent phosphodiesterase IVb inhibitors from nitroethane, isovanillin, and ethyl vinyl ether was developed. The compounds obtained are the derivatives of hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one and tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one. The strategy proposed involves silylation of six-membered cyclic nitronates as a key step leading to 5,6-dihydro-4H-1,2-oxazines with the group CH2FG (FG = N3 or OH) at the C(3) atom.

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Authors and Affiliations

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

    P. A. Zhmurov, A. A. Tabolin, A. Yu. Sukhorukov, M. S. Klenov, Yu. A. Khomutova, S. L. Ioffe & V. A. Tartakovsky

  2. Moscow Chemical Lyceum No. 1303, 4 Tamozhennyi proezd, 111033, Moscow, Russian Federation

    A. V. Lesiv

Authors
  1. P. A. Zhmurov
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  2. A. A. Tabolin
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  3. A. Yu. Sukhorukov
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  4. A. V. Lesiv
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  5. M. S. Klenov
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  6. Yu. A. Khomutova
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  7. S. L. Ioffe
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  8. V. A. Tartakovsky
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Corresponding author

Correspondence to A. Yu. Sukhorukov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 80th birthday.

For Part 1, see Ref. 1a.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2343–2348, November, 2011.

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Zhmurov, P.A., Tabolin, A.A., Sukhorukov, A.Y. et al. Synthesis of phosphodiesterase IVb inhibitors 2. Stereoselective synthesis of hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one and tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one derivatives. Russ Chem Bull 60, 2390–2395 (2011). https://doi.org/10.1007/s11172-011-0367-5

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  • DOI: https://doi.org/10.1007/s11172-011-0367-5

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