Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Synthesis of a New Dioxaspiro[bicyclo[3.3.1]nonane-oxabicyclo[6.2.0]deca- 1(10),8-dien-4-one Derivative Using Some Chemical Strategies

Author(s): Figueroa-Valverde Lauro*, Rosas-Nexticapa Marcela, Lopez-Ramos Maria, Diaz Cedillo Francisco, Mateu-Armand Virginia, Garcimarero-Espino E. Alejandra, Borges-Ballote Yaritza and Ortiz-Ake Yazmin

Volume 17, Issue 5, 2020

Page: [393 - 402] Pages: 10

DOI: 10.2174/1570178617666191116123359

Price: $65

Abstract

There are several protocols for the preparation of bicyclic derivatives; however, some methods use dangerous and require special conditions. The aim of this study was to synthesize a new Dioxaspiro[ bicyclo[3.3.1]nonane-oxabicyclo[6.2.0]-deca-1(10), 8-dien-4-one (compound 8). Compound 8 was prepared using some reactions such as; i) etherification, ii) reduction, iii) amidation, iv) imination and v) 2+2 addition. The chemical structure of 8 and its intermediaries were completely characterized by spectroscopic techniques and elemental analysis. The synthesis showed a yield of 85% for compound 8. In this study, an easy method for the preparation of compound 8 is reported.

Keywords: Steroid, bicyclo, dioxaspiro, etherification, reduction, dienone.

Graphical Abstract

[1]
Magnus, P.; Exon, C.; Albaugh, R. Tetrahedron Lett., 1985, 41, 5861-5869.
[http://dx.doi.org/10.1016/S0040-4020(01)91425-5]
[2]
Singh, S.K.; Kumar, R.; Wengel, J. J. Org. Chem., 1998, 63(18), 6078-6079.
[http://dx.doi.org/10.1021/jo9806658] [PMID: 11672223]
[3]
Cimarusti, C.; Wolinsky, J. J. Am. Chem. Soc., 1968, 90, 113-120.
[http://dx.doi.org/10.1021/ja01003a020]
[4]
Greshock, T.J.; Funk, R.L. J. Am. Chem. Soc., 2002, 124(5), 754-755.
[http://dx.doi.org/10.1021/ja0123554] [PMID: 11817942]
[5]
Filippini, M.; Faure, R.; Rodriguez, J. J. Org. Chem., 1995, 60, 6872-6882.
[http://dx.doi.org/10.1021/jo00126a044]
[6]
Cao, C.L.; Sun, X.L.; Kang, Y.B.; Tang, Y.; Tang, Y. Org. Lett., 2007, 9(21), 4151-4154.
[http://dx.doi.org/10.1021/ol701669b] [PMID: 17867691]
[7]
Ishikawa, T.; Kadoya, R.; Arai, M.; Takahashi, H.; Kaisi, Y.; Mizuta, T.; Yoshikai, K.; Saito, S. J. Org. Chem., 2001, 66(24), 8000-8009.
[http://dx.doi.org/10.1021/jo010325d] [PMID: 11722197]
[8]
Trost, B.M.; McDougall, P.J.; Hartmann, O.; Wathen, P.T. J. Am.Chem. Soc.,, 2008, 130(45), 14960-14961.
[http://dx.doi.org/10.1021/ja806979b] [PMID: 18937462]
[9]
Stork, G.; Landesman, H. J. Am. Chem. Soc., 1956, 79, 5129-5130.
[http://dx.doi.org/10.1021/ja01600a088]
[10]
Liu, H.; Ho, L.; Lai, H. Can. J. Chem., 1981, 59, 1685-1688.
[http://dx.doi.org/10.1139/v81-251]
[11]
Veselovsky, V.; Zhuzbaev, B.; Turdybekov, K.; Adekenov, S.; Struchkov, Y.; Moiseenkov, A. Russ. Chem. Bull., 1993, 42, 106-110.
[http://dx.doi.org/10.1007/BF00699987]
[12]
Fickes, G.; Kemp, K. J. Chem. Soc. Chem. Commun., 1973, 3, 84-85.
[http://dx.doi.org/10.1039/C39730000084]
[13]
Quach, T.D.; Batey, R.A. Org. Lett., 2003, 5(8), 1381-1384.
[http://dx.doi.org/10.1021/ol034454n] [PMID: 12688764]
[14]
Harkal, S.; Kumar, K.; Michalik, D.; Zapf, A.; Jackstell, R.; Rataboul, F.; Beller, M. Tetrahedron Lett., 2005, 46, 3237-3240.
[http://dx.doi.org/10.1016/j.tetlet.2005.03.033]
[15]
Dueno, E.; Chu, F.; Kim, S.; Jung, K. Tetrahedron Lett., 1999, 40, 1843-1846.
[http://dx.doi.org/10.1016/S0040-4039(99)00083-0]
[16]
Fuhrmann, E.; Talbiersky, J. Org. Process Res. Dev., 2005, 9, 206-211.
[http://dx.doi.org/10.1021/op050001h]
[17]
Mollavali, M.; Yaripour, F.; Atashi, H.; Sahebdelfar, S. Ind. Eng. Chem. Res., 2008, 47, 3265-3273.
[http://dx.doi.org/10.1021/ie800051h]
[18]
Palomo, C.; Oiarbide, M.; López, R.; Gómez, E. Chem. Commun. (Camb.), 1998, 19, 2091-2092.
[http://dx.doi.org/10.1039/a805783d]
[19]
Figueroa, L.; Diaz, F.; Rosas, M.; García, E.; Pool, E. Lett. Org. Chem., 2015, 6, 394-401.
[20]
Chopade, P.R.; Prasad, E.; Flowers, R.A. J. Am. Chem. Soc., 2004, 126(1), 44-45.
[http://dx.doi.org/10.1021/ja038363x] [PMID: 14709051]
[21]
Cheung, F.K.; Clarke, A.J.; Clarkson, G.J.; Fox, D.J.; Graham, M.A.; Lin, C.; Crivillé, A.L.; Wills, M. Dalton Trans., 2010, 39(5), 1395-1402.
[http://dx.doi.org/10.1039/B915932K] [PMID: 20104368]
[22]
Willems, J.; Dommerholt, F.; Hammink, J.; Vaarhorst, A.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett., 1995, 36, 603-606.
[http://dx.doi.org/10.1016/0040-4039(94)02313-Z]
[23]
Barden, M.; Schwartz, J. J. Org. Chem., 1995, 60, 5963-5965.
[http://dx.doi.org/10.1021/jo00123a039]
[24]
Chaikin, S.; Brown, W. J. Am. Chem. Soc., 1949, 71, 122-125.
[http://dx.doi.org/10.1021/ja01169a033]
[25]
Nordstrøm, L.U.; Vogt, H.; Madsen, R. J. Am. Chem. Soc., 2008, 130(52), 17672-17673.
[http://dx.doi.org/10.1021/ja808129p] [PMID: 19061316]
[26]
Cho, S.H.; Yoo, E.J.; Bae, I.; Chang, S. J. Am. Chem. Soc., 2005, 127(46), 16046-16047.
[http://dx.doi.org/10.1021/ja056399e] [PMID: 16287290]
[27]
Ghosh, S.; Muthaiah, S.; Zhang, Y.; Xu, X.; Hong, S. Adv. Synth. Catal., 2009, 351, 2643-2649.
[http://dx.doi.org/10.1002/adsc.200900482]
[28]
Shimizu, K.; Ohshima, K. Satsuma. Chemistry, 2009, 15, 9977-9980.
[http://dx.doi.org/10.1002/chem.200901896] [PMID: 19760737]
[29]
Figueroa, L.; Diaz, F.; García, E.; Pool, E.; López, M. Bulg. Chem.Commun, 2013, 45, 71-76.
[30]
Benincori, T.; Brenna, E.; Sannicolo, F. J. Chem. Soc. Perkin 1,, 1993, 6, 675-679.
[31]
Weinmann, H.; Harre, M.; Koenig, K.; Merten, E.; Tilstam, U. Tetrahedron Lett., 2002, 43, 593-595.
[http://dx.doi.org/10.1016/S0040-4039(01)02226-2]
[32]
Gracias, V.; Darczak, D.; Gasiecki, A.; Djuric, S. Tetrahedron Lett., 2005, 46, 9053-9056.
[http://dx.doi.org/10.1016/j.tetlet.2005.10.090]
[33]
Zeng, R.S.; Zou, J.P.; Zhi, S.J.; Chen, J.; Shen, Q. Org. Lett., 2003, 5(10), 1657-1659.
[http://dx.doi.org/10.1021/ol030024l] [PMID: 12735745]
[34]
Imada, Y.; Nakamura, M. J. Org. Chem., 1994, 59, 2282-2284.
[http://dx.doi.org/10.1021/jo00088a004]
[35]
Pravin, L.; Madavu, S.; Sarabindu, R.; Mannepalli, K.; Balasubramanian, S.; Ratanesh, S.; Sukla, B. Org. Biomol. Chem., 2009, 7, 85-93.
[http://dx.doi.org/10.1039/B815398A] [PMID: 19081950]
[36]
Yadav, J.; Reddy, B.; Gopal, A.; Patil, K. Tetrahedron Lett., 2009, 50, 3493-3496.
[http://dx.doi.org/10.1016/j.tetlet.2009.03.014]
[37]
Bisai, A.; Singh, V.K. Org. Lett., 2006, 8(11), 2405-2408.
[http://dx.doi.org/10.1021/ol060793f] [PMID: 16706537]
[38]
Crossland, R.; Kenneth, S. J. Org. Chem., 1970, 35, 3195-3196.
[http://dx.doi.org/10.1021/jo00834a087]
[39]
Ping, H.; Yang, F.; Tang, J.; He, M. Green Chem., 2003, 5, 38-39.
[http://dx.doi.org/10.1039/b209248b]
[40]
Erlanger, B.F.; Borek, F.; Beiser, S.M.; Lieberman, S. J. Biol. Chem., 1957, 228(2), 713-727.
[PMID: 13475354]
[41]
Abele, S.; Inauen, R.; Spielvogel, D.; Moessner, C. J. Org. Chem., 2012, 77(10), 4765-4773.
[http://dx.doi.org/10.1021/jo3005638] [PMID: 22551166]
[42]
Kikaš, I.; Škorić, I.; Marinić, Ž.; Kulyk, M. Tetrahedron Lett., 2010, 66, 9405-9414.
[http://dx.doi.org/10.1016/j.tet.2010.09.093]
[43]
Sarel, S.; Langbeheim, M. J. Chem. Soc. Chem. Commun., 1977, 22, 827-828.
[http://dx.doi.org/10.1039/c39770000827]
[44]
Lin, G.Y.; Yang, C.Y.; Liu, R.S. J. Org. Chem., 2007, 72(18), 6753-6757.
[http://dx.doi.org/10.1021/jo0707939] [PMID: 17676805]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy