Abstract
A general methodology for the stereoselective synthesis of compounds of the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane series was developed. The strategy includes allylboration of aromatic aldehydes with 1,6-bis(dialkylboryl)-2,4-hexadiene, ozonolysis of the thus obtained 1,4-diaryl-2,3-divinyl-1,4-diols, and subsequent intramolecular cyclization. This methodology was used for obtaining the naturally occurring lignans of the furofuran series, viz., diaeudesmin, diayangambin, epiasarinin, epieudesmin, epiyangambin, and asarinin.
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References
R. S. Ward, Nat. Prod. Rep. 1995, 12, 183.
W. D. MacRae, G. H. N. Towers, Phytochemistry, 1984, 23, 1207.
S. Iwakami, Jin-Bin Wu, Y. Ebizuka, U. Sankawa, Chem. Pharm. Bull., 1992, 40(5), 1196.
M. W. Biavatti, P. C. Vieira, M. Fa’tima G. F. da Silva, J. B. Fernandes, Ana L. G. Degani, Q. B. Cass, A. B. Schefer, A. G. Ferreira, Phytochem. Anal., 2001, 12, 64.
A. Pelter, R. S. Ward, D. J. Watson, P. Collins, I. T. Kay, J. Chem. Soc., Perkin Trans., 1982, 1, 175
R. C. D. Brown, J. D. Hinks, Chem. Commun. 1998, 17, 1895
R. C. D. Brown, C. J. R. Bataille, G. Bruton, J. D. Hinks, N. A. Swain, J. Org. Chem, 2001, 66, 6719.
R. C. D. Brown, C. J. R. Bataille, G. Bruton, J. D. Hinks, N. A. Swain, J. Org. Chem., 2001, 66, 6719.
D. J. Aldous, A. J. Dalencüon, P. G. Steel, Org. Lett., 2002, 4, 1159.
M. Pohmakotr, A. Pinsa, T. Mophuang, P. Tuchinda, S. Prabpai, P. Kongsaeree, V. Reutrakul, J. Org. Chem., 2006, 71, 386.
A. N. Anfimov, S. Yu. Erdyakov, M. E. Gurskii, A. V. Ignatenko, K. A. Lyssenko, Yu. N. Bubnov, Mendeleev Commun., 2011, 21, 1.
M. E. Gurskii, A. V. Geiderikh, A. V. Ignatenko, Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 1993, 160 [Russ. Chem. Bull. (Engl. Transl.), 1993, 42, 144.
R. E. Valters, F. Fulop, D. Korbonits, Advances Heterocyclic Chem., 1995, 64, 251.
G. A. Molander, C. Kenny, J. Org. Chem., 1988, 53, 2134.
M. Watanabe, N. Harada, J. Org. Chem., 1995, 60, 7372.
S. G. Van Ornum, R. M. Champeau, R. Pariza, Chem. Rev., 2006, 106, 2990.
S. D. Razumovskii, Yu. Z. Yur’ev, Neftekhimiya [Petrochemistry], 1966, 6, 737 (in Russian)
S. D. Razumovskii, G. A. Zaikov, Ozon i ego reaktsii s organicheskimi soedineniyami [Ozone and Its Reactions with Organic Compounds], Nauka, Moscow, 1974, 322 pp. (in Russian).
A. Pelter, R. S. Ward, P. Collins, R. Venkateswarlu, I. T. Kay, J. Chem. Soc., Perkin Trans., 1985, 587.
A. Pelter, R. S. Ward, R. Venkateswarlu, C. Kamakshi, Tetrahedron, 1992, 48, 7209.
D. A. Olmedo, N. Nakamura, M. Hattori, M. D. Correa, P. N. Solis, M. P. Gupta, Lignanos anti-Aedes aegupti de Productos Naturales y sus Aplicaciones (Chile, 1998, 1–4 de Deciembre).
E. J. De Leon, D. A. Olmedo, P. N. Solis, M. P. Gupta, M. C. Terencio, Planta Med., 2002, 68, 1128.
A. Pelter, R. S. Ward, Tetrahedron, 1976, 32, 2783.
A. Pelter, R. S. Ward, Chemistry of Lignans, Ed. C. B. S. Rao, Andhra University Press, 1978, Ch. 7.
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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2291–2297, November, 2011.
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Anfimov, A.N., Erdyakov, S.Y., Gurskii, M.E. et al. Stereospecific synthesis of endo-endo-3,7-dioxabicyclo[3.3.0]octane lignans using 1,6-bis(dipropylboryl)-2,4-hexadiene. Russ Chem Bull 60, 2336–2342 (2011). https://doi.org/10.1007/s11172-011-0358-6
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DOI: https://doi.org/10.1007/s11172-011-0358-6