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Synthesis of ent-crotonadiol and compounds related to it from (+)-larixol

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Chemistry of Natural Compounds Aims and scope

A new synthesis of 13E-ent-crotonadiol and its 13Z-isomer from 6a-acetoxy-14,15-bis-norlabd-8(17)-en13-one is described. A mixture of methyl esters of 13E- and 13Z-6a-acetoxylabd-8(17),13-dien-15-oic and 13E- and 13Z-6a-hydroxylabd-8(17),13-dien-15-oic acids was formed by its reaction with trimethylphosphonoacetate. Mixtures of 13E- and 13Z-6a-hydroxylabd-8(17),13-dien-15-oic acids were formed by hydrolysis of this mixture. These were separated, methylated, and reduced by LiAlH4 to give the pure 13E- and 13Z-crotonadiols in 64 and 16% yields, respectively. The two known syntheses of crotonadiol from (+)-larixol were reproduced. It was shown that they produced only 13E-crotonadiol.

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References

  1. B. T. Ngadjui, G. G. Folefoc, F. Keumedjio, E. Dengo, B. L. Sodengam, and J. D. Connolly, Phytochemistry, 51, 171 (1999).

    Article  CAS  Google Scholar 

  2. A. Salatino, M. L. F. Salatino, and G. Negri, J. Braz. Chem. Soc., 18, 11 (2007).

    Article  CAS  Google Scholar 

  3. B. H. Yang, W. D. Zhang, Z. B. Gu, T. Z. Li, C. Zhang, and Y. Zhou, Chin. Chem. Lett., 15, 919 (2004)

    CAS  Google Scholar 

  4. J. Haeuser, Bull. Soc. Chim. Fr., 9, 2645 (1965).

    Google Scholar 

  5. M. A. Golikova, T. V. Romanchenko, V. I. Bolshakova, E. N. Shmidt, V. A. Pentegova, G. M. Maksimov, and C. I. Matveev, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., 3, 109 (1988).

    Google Scholar 

  6. V. Kulcitki, N. Ungur, and P. F. Vlad, Tetrahedron, 54, 11925 (1988).

    Article  Google Scholar 

  7. P. Martes, P. Perfetti, J. P. Zahra, and B. Waegell, Tetrahedron Lett., 32, 765 (1991).

    Article  Google Scholar 

  8. J. P. Zahra, F. Chauvet, I. Coste-Maniere, P. Martres, P. Perfetti, and B. Waegell, Bull. Soc. Chim. Fr., 134, 1001 (1997).

    CAS  Google Scholar 

  9. W. Sandermann and K. Bruns, Chem. Ber., 99, 2835 (1966).

    Article  CAS  Google Scholar 

  10. C. Morin and N. Nedjar, Tetrahedron Lett., 37, 4705 (1996).

    Article  CAS  Google Scholar 

  11. M. G. Bolster, B. J. M. Jansen, and A. de Groot, Tetrahedron, 57, 5663 (2001).

    Article  CAS  Google Scholar 

  12. M. G. Bolster, B. M. F. Lagnel, B. J. M. Jansen, C. Morin, and A. de Groot, Tetrahedron, 57, 8369 (2001).

    Article  CAS  Google Scholar 

  13. W. Sandermann and K. Bruns, Naturwissenschaften, 52, 560 (1965).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors from P. Poni Institute are grateful for support by Project No. 264115 (STREAM), which is an integral part of European Project FP7-REGPOT-2010-1.

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Authors and Affiliations

  1. Institute of Chemistry, Academy of Sciences of Moldova, MD-2028, Chisinau, Moldova

    P. F. Vlad, A. Chokyrlan, M. N. Koltsa, A. N. Barba, K. Edu & A. Byryyak

  2. P. Poni Institute of Macromolecular Chemistry, Roumanian Academy of Sciences, Aleea G. G. Voda, 41, RO-700487, Iasi, Roumania

    A. Chokyrlan, A. Nikolescu & K. Deleanu

  3. C. D. Nenitzescu Institute of Organic Chemistry, Roumanian Academy of Sciences, Splaiul Independentei, 202B, RO-35-98, Bucharest, Roumania

    A. Nikolescu & K. Deleanu

  4. University of Trento, Via Sommarive, 14, Povo, Italy

    M. D’Ambrosio & A. Mari

Authors
  1. P. F. Vlad
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  2. A. Chokyrlan
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  3. M. D’Ambrosio
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  4. M. N. Koltsa
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  5. A. N. Barba
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  6. K. Edu
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  7. A. Byryyak
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  8. A. Nikolescu
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  9. A. Mari
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  10. K. Deleanu
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Corresponding author

Correspondence to P. F. Vlad.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 356–361, May–June, 2011.

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Vlad, P.F., Chokyrlan, A., D’Ambrosio, M. et al. Synthesis of ent-crotonadiol and compounds related to it from (+)-larixol. Chem Nat Compd 47, 397 (2011). https://doi.org/10.1007/s10600-011-9943-z

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  • DOI: https://doi.org/10.1007/s10600-011-9943-z

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