Synthesis of substituted allyl acetates from heterocyclic dienes by Pd-promoted arylation-acetoxylation cascade

Milena R. Simić, Miloš R. Petković, Predrag M. Jovanović, Gordana D. Tasić, Vladimir M. Savić

Abstract


Pd-catalysed arylation/acetoxylation cascade, the methodology previously reported by our laboratory, was applied in the functionalisation of unsymmetrical dienes. Both explored classes of compounds, isoquinoline and b-carboline derived dienes, afforded single regioisomers. Although further improvements of the process are necessary, primarily due to lower yields, described functionalisation of the studied compounds might be useful in the synthesis of emetine and related naturally occurring compounds. 


Keywords


heterocycles, synthesis, emetine-like compounds

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References


D. Liu and X. Yu, Tetrahedron Lett. 53 (2012) 2177

K. Afarinkia and J. Berna-Canovas, Tetrahedron Lett. 41 (2000) 4955

R. L. Funk, J. B. Stallman and J. A. Wos, J. Am. Chem. Soc. 115 (1993) 8847

P. Chouthaiwale, P. Karabal, G. Suryavanshi and A. Sudalai, Synthesis 2010 (2010) 3879

E. Falkowska, F. Suzenet, P. Jubault, J.-P. Bouillon and X. Pannecoucke, Tetrahedron Lett. 55 (2014) 4833

F. Li, C. Shen, J. Zhang, L. Wu, X. Zhuo, L. Ding and G. Zhong, Adv. Synth. Catal. 358 (2016) 3932

R. Manikandan, P. Madasamy and M. Jeganmohan, Chem - Eur. J. 21 (2015) 13934

S. Jayakumar, M. Prakash, K. Balaraman and V. Kesavan, Eur. J. Org. Chem. 2014 (2014) 606

M. Kim, J. Park, S. Sharma, S. Han, S. H. Han, J. H. Kwak, Y. H. Jung and I. S. Kim, Org. Biomol. Chem. 11 (2013) 7427

W. Yu, W. Zhang, Y. Liu, Z. Liu and Y. Zhang, Org. Chem. Front. 4 (2017) 77

H. Dai, C. Yu, Z. Wang, H. Yan and C. Lu, Org. Lett. 18 (2016) 3410

S. W. Kim, W. Lee and M. J. Krische, Org. Lett. 19 (2017) 1252

S. Mizuno, S. Terasaki, T. Shinozawa and M. Kawatsura, Org. Lett. 19 (2017) 504

X. Wang, X. Wang, Z. Han, Z. Wang and K. Ding, Angew. Chem. Int. Ed. 56 (2017) 1116

P. Dhankher, L. Benhamou and T. D. Sheppard, Chem. - Eur. J. 20 (2014) 13375

C. Amatore, S. Gamez, A. Jutand, G. Meyer and L. Mottier, Electrochimica Acta 46 (2001) 3237

B. M. Trost, V. Ehmke, B. M. O’Keefe and D. A. Bringley, J. Am. Chem. Soc. 136 (2014) 8213

L.-Y. Chen, X.-Y. Yu, J.-R. Chen, B. Feng, H. Zhang, Y.-H. Qi and W.-J. Xiao, Org. Lett. 17 (2015) 1381

Y. Horino, A. Aimono and H. Abe, Org. Lett. 17 (2015) 2824

G. Hamasaka, F. Sakurai and Y. Uozumi, Tetrahedron 71 (2015) 6437

X.-Q. Hao, Y.-N. Dong, B. Gao, K. Li, X.-M. Zhao, Y. Xu and M.-P. Song, Tetrahedron Asymmetry 26 (2015) 1360

M. Billamboz, F. Mangin, N. Drillaud, C. Chevrin-Villette, E. Banaszak-Léonard and C. Len, J. Org. Chem. 79 (2014) 493

H. Yin, D. U. Nielsen, M. K. Johansen, A. T. Lindhardt and T. Skrydstrup, ACS Catal. 6 (2016) 2982

Y. Kobayashi, S. Yoshida and Y. Nakayama, Eur. J. Org. Chem. 2001 (2001) 1873

S. Cheng and S. Yu, Org. Biomol. Chem. 12 (2014) 8607

S. Chandrasekhar and C. R. Reddy, Tetrahedron Asymmetry 13 (2002) 261

T. Mitsudome, T. Umetani, N. Nosaka, K. Mori, T. Mizugaki, K. Ebitani and K. Kaneda, Angew. Chem. Int. Ed. 45 (2006) 481

X. Xing, N. R. O’Connor and B. M. Stoltz, Angew. Chem. Int. Ed. 54 (2015) 11186

H. A. Malik, B. L. H. Taylor, J. R. Kerrigan, J. E. Grob, K. N. Houk, J. Du Bois, L. G. Hamann and A. W. Patterson, Chem. Sci. 5 (2014) 2352.

A. N. Campbell, P. B. White, I. A. Guzei and S. S. Stahl, J. Am. Chem. Soc. 132 (2010) 15116

T. Diao and S. S. Stahl, Polyhedron 84 (2014) 96

S. Husinec, M. Jadranin, R. Markovic, M. Petkovic, V. Savic and N. Todorovic, Tetrahedron Lett. 51 (2010) 4066

S. Husinec, M. Petkovic, V. Savic and M. Simic, Synthesis 44 (2012) 399

L. F. Tietze, N. Rackelmann and I. Müller, Chem. – Eur. J. 10 (2004) 2722

E. S. Akinboye and O. Bakare, Open Nat. Prod. J., 2011, 4.

The Alkaloids: Chemistry and Pharmacology, Academic Press, 1984.

C. R. Johnson and D. S. Dhanoa, J. Org. Chem. 52 (1987) 1885

A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar and J.-E. Bäckvall, Synlett 2001 (2001) 0923

A. Sunderkötter, S. Lorenzen, R. Tacke and P. Kraft, Chem. - Eur. J. 16 (2010) 7404

Y. Takashima and Y. Kobayashi, J. Org. Chem. 74 (2009) 5920

S. Husinec, V. Savic, M. Simic, V. Tesevic and D. Vidovic, Tetrahedron Lett. 52 (2011) 2733

M. R. Simić, A. Damjanović, M. Kalinić, G. Tasić, S. Erić, J. Antić-Stanković and V. Savić, J. Serb. Chem. Soc. 81 (2016) 103.




DOI: http://dx.doi.org/10.2298/JSC170317046S

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