Investigation of Synthesis of Functionally Substituted Endiines and Their Chemical and Microbiological Conversion

M. G. Veliyev, M. A. Salmanov, M. I. Shatirova, S. R. Aliyeva, L. N. Bunyatova

Institute of Microbiology of Azerbaijan National Academy of Sciences, Baku, Azerbaijan.
Institute of Polymer Materials of Azerbaijan National Academy of Sciences, Sumgayit, Azerbaijan.

DOI: 10.4236/ijoc.2013.33A002                

Abstract

The methods of preparation of endiine and endiallene diols by interaction of cis-1,4-dibrombutene and cis-1,4-dichlor-rbutene with monosubstituted acetylene alcohols in presence of the catalytic systems consisting of one-iodide copper, triethylamine and K₂СО₃ in a medium of dimethylformamide have been developed. It has been shown that unlike 1,4-dibrombutene, the nucleophilic substitution reaction with 1,4-dichlorbutene proceeds by acetylene-allene isomerization with formation of endiallene diols. It has been established that the endiine diols can be used in thin organic synthesis (in the reactions of oxidation, splitting, dehydration, epoxidation, hydrolysis, 1,2-cycloaddition and hypochlorination) with the aim of preparation of practically useful substances. It has been revealed during hydrolysis of epoxide compounds by the chemical and microbiological methods that in the course of microbiological hydrolysis (Aspеrgillus niger), the optically active trans-structured diols are formed.

Keywords

Substitution Reaction; Endiine Diols; Chemical Methods; Oxidation of Diols; Hydrolysis of Epoxydiine; Microbiological Hydrolysis; Micromycetes

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	I. A. Maretina and B. A. Trofimov, “Endiine Antibiotics and Their Models: New Possibilities of Chemistry of Acetylene,” Uspekhii Khimii, Vol. 75, No. 9. 2006, pp. 913-935.
[2]	G. Yu. Ishmuratov, V. A. Vydrina, G. V. Nasibullina, A. G. Tolstikov and G. A. Tolstikov, “Natural Aliphatic Unsaturated Acids Containing Oxygen Functions. Synthesis and Biological Activity,” Chemistry of Vegetable Raw Materials, No. 3, 2012, pp. 5-36.
[3]	N. Yoshimura, A. Momotake, Y. Shinohara, Y. Nishimura and T. Arai, “Enediyne-Type Dendrimers with Bensyl. Ether Dondrous,” Bulletin of the Chemical Society of Japan, Vol. 80, No. 10, 2007, pp. 1995-2000.
[4]	Y.-F. Lu, C. W. Harwig and A. G. Fallis, “Taxamycins: A New Enediyne Family Constructed from Versatile Disilyl-Substituted Building,” The Journal of Organic Chemistry, Vol. 58, No. 16, 1993, pp. 4202-4204.
[5]	K. Iguchi, М. Kitadе, T. Kashiwagi and Y. Yamada, “Structure and Synthesis of Petrosynes, New Acetylenic Enol Ether Glycerides from the Okinawan Marine Sponge of the Genus Petrosia,” The Journal of Organic Chemistry, Vol. 58, No. 21, 1993, pp. 5690-5698.
[6]	A. E. Wright, O. J. McConnel, S. Kohmoto, M. S. Lui, W. Thomson and K. M. Snader, “Duryne, a New Cytotoxic Agent from the Marine Sponge Cribrochalina Dura,” Tetraherdon Letters, Vol. 28, No. 13, 1987, pp. 1377-1380.
[7]	K. Mizukoshi, S. Okada, T. Kimura, S. Shimada and H. Matsuda, “Synthesis and Solid-State Polymerization of Triyne and Enediyne Derivatives with Similar π-Conjugated Structures,” Bulletin of the Chemical Society of Japan, Vol. 81, No. 8, 2008, pp. 1028-1037.
[8]	I. A. Maretina, “Strategy of Design of Endiines and Enyne-Allenes,” ZHOKH, Vol. 78, No. 2, 2008, pp. 244-278.
[9]	J. K. Yong and J. S. Moore, “Modern Acetylene Chemistry,” VCH, Weinheim, 1995, p. 415.
[10]	F. J. Schoenen, J. F. Porco Jr. and S. L. Schreiber, G. D. Van Duyne and J. Clardy, “Synthesis and Crystallographic Analysis of a Bicyclic Core Related to the Esperamicin/Calichemicin Aglycones,” Tetraherdon Letters, Vol. 30, No. 29, 1989, pp. 3765-3768.
[11]	J. W. Grissom and T. L. Calkins, “Kinetic and Mechanistic Studies of the Tandem Enediyne-Radical Cyclization,” The Journal of Organic Chemistry, Vol. 58, No. 20, 1993, pp. 5422-5427.
[12]	M. Ahmed, G. C. Barley, M. T. W. Hearn, E. R. H. Jones, V. Thaller and J. A. Yates, “Natural Acetylenes. Part XLIII. Polyacetylenes from Cultures of the Fungus Fistulina Pallid,” Journal of the Chemical Society, Perkin Transactions, No. 16, 1974, pp. 1981-1994.
[13]	B. Konig and W. Pitsch, “Synthesis, Structure, and Reactivity of Enediyne Macrocycles,” The Journal of Organic Chemistry, Vol. 61, No. 13, 1996, pp. 4258-4261.
[14]	E. Quifioa and P. Crews, “Melynes, Polyacetylene Constituents from a Vanuatu Marine Sponge,” Tetrahedron Letters, Vol. 29, No. 17, 1988, pp. 2037-2040.
[15]	V. F. Kucherova, M. V. Mavrov and A. R. Dzerzhinskiy, “Natural Polyacetylene Compounds,” Nauka, M., 1972, 392 p.
[16]	I. A. Maretina, “Porphyrin-Ethyl Blocks: Synthesis, Design, Application,” ZHOKH, Vol. 79, 2005, pp. 1187-1224.
[17]	G. Nakaminami, “Structure and Biogenesis of Natural Acetylene Compounds,” Uspekhii Khimii, Vol. 34, 1965, pp. 503-529.
[18]	M. Ji, H. O’Dowd, B. M. Rosen and A. G. Myers, “Enantioselective Synthesis of N1999A2,” Journal of the American Chemical Society, Vol. 128, No. 46, 2006, pp. 14825-14827. http://dx.doi.org/10.1021/ja0662467
[19]	K. C. Nicolaou, “Unique Compounds: Enediynes Are Potent Cancer Killers,” Journal of the National Cancer Institute, Vol. 85, No. 1, 1993, pp. 8-9. http://dx.doi.org/10.1093/jnci/85.1.8
[20]	M. A. Salmanov, M. G. Veliyev and P. Z. Muradov, “Acetylene Compounds of Natural Origin: Sources of Isolation and Basic Chemical Conversions,” Works of the Institute of Microbiology of Azerbaijan National Academy of Sciences, Elm, Baku, 2005, pp.171-182.
[21]	M. I. Shatirova, “Diss. cand. chem. Sci,” ASOA, Baku, 1999, 159 p
[22]	M. A. Salmanov, M. G. Veliyev and P. Z. Muradov, “Basidiomycetes-Perspective Producers of Polyacetylene Compounds,” Izv. ANAS. Ser. biolog. sci, No. 3-4, 2004, pp. 142-149.
[23]	S .R. Alieva, M. G. Veliyev, E. I. Ismailov, G. G. Yagubova and P. Z. Muradov, “Biosynthesis of Polyacetylene Compounds by Basidial Fungi,” Journal of Immunopathology, Allergology, Infectology, No. 2. 2009, pp. 158-159.
[24]	M. Veliyev, M. Shatirova, O. Askerov, A. Chalabiyeva and A. Mamedova, “Synthesis of Functionally Substituted Enediines,” 21 Ulusal kimya kongresi, Inonü Universitesic, Malatya, 23-27 August 2007, 113p.
[25]	M. G. Veliyev, M. I. Shatirova and A. F. Mamedova, “Synthesis and Investigation of Functionally Substituted Enediines,” 3rd International Scient Conference, Baku, 14-16 December 2005, pp. 84-87.
[26]	R. Silverstein, G. Bassler and T. Moryl, “Spectrometric Identification of Organic Compounds,” Mir, M., 1977, 590 p.
[27]	A. Gordon and R. Ford, “Chemists’ Satellite,” Mir, M., 1974, 541p.
[28]	M. A. Salmanov, M. G. Veliyev and S. R. Alieva, “Biodestruction and Biotransformation in Organic Synthesis,” Elm, Baku, 2011, 200 p.