Facile Strategy to Access the Indolo[2,3-a]quinolizidine Framework: Synthetic Study on Tangutorine

Chada Raji Reddy; Kamalkishor Warudikar; Bellamkonda Latha

doi:10.1055/s-0039-1690004

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(19): 3715-3722
DOI: 10.1055/s-0039-1690004

paper

Facile Strategy to Access the Indolo[2,3-a]quinolizidine Framework: Synthetic Study on Tangutorine^[1]

Chada Raji Reddy∗

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India eMail: rajireddy@iict.res.in

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

,

Kamalkishor Warudikar

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India eMail: rajireddy@iict.res.in

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

,

Bellamkonda Latha

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India eMail: rajireddy@iict.res.in

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

^§ These authors have contributed equally to this manuscript.

Abstract

An asymmetric synthetic approach to indolo[2,3-a]quinolizidine framework has been developed involving Horner–Wadsworth–Emmons olefination and reductive amination as the key steps. Further, the developed strategy was explored towards the synthesis of tangutorine using Evans aldol reaction for the preparation of desired aldehyde.

Key words

indolo[2,3-a]quinolizidine - Horner–Wadsworth–Emmons reaction - piperidine - tangutorine

Volltext

Referenzen

References
1 CSIR-IICT Communication No. IICT/Pubs./2019/167.

2a Herbert RB. The Monoterpenoid Indole Alkaloids . In The Chemistry of Heterocyclic Compounds, Supplement to Vol. 25, Part 4. Saxon JE. Wiley-Interscience; New York: 1994. Chap. 1
2b Saxon JE. The Monoterpenoid Indole Alkaloids . In The Chemistry of Heterocyclic Compounds, Supplement to Vol. 25, Part 4. Saxon JE. Wiley-Interscience; New York: 1994. Chap. 8
2c Saxon JE. In The Alkaloids, Vol. 50. Cordell GA. Academic Press; New York: 1998
2d Saxon JE. In The Alkaloids, Vol. 51. Cordell GA. Academic Press; New York: 1998
2e Toyota M, Ihara M. Nat. Prod. Rep. 1998; 15: 327
2f Scholz U, Winterfeldt E. Nat. Prod. Rep. 2000; 17: 349

3 Duan J.-A, Williams ID, Che C.-T, Zhou R.-H, Zhao S.-X. Tetrahedron Lett. 1999; 40: 2593
4 Liu BP. L, Chong EY. Y, Cheung FW. K, Duan J.-A, Che C-T, Liu WK. Biochem. Pharmacol. 2005; 70: 287
5 Putkonen T, Tolvanen A, Jokela R. Tetrahedron Lett. 2001; 42: 6593
6 Luo S, Zificsak CA, Hsung RP. Org. Lett. 2003; 5: 4709
7 Putkonen T, Tolvanen A, Jokela R, Caccamesec S, Parrinello N. Tetrahedron 2003; 59: 8589
8 Salame R, Gravel E, Leblanc K, Poupon E. Org. Lett. 2009; 11: 1891

9a Nemoto T, Yamamoto E, Franzen R, Fukuyama T, Wu R, Fukamachi T, Kobayashi H, Hamada Y. Org. Lett. 2010; 12: 872
9b Zhang S, Pozo J-D, Romiti F, Yucheng M, Torker S, Hoveyda A. Science 2019; 364: 45

10a Shengjun L, Zhao J, Zhai H. J. Org. Chem. 2004; 69: 4548
10b Wilkinson J-A, Ardes-Guisot N, Duckia S, Leonard J. Tetrahedron Lett. 2005; 46: 8053
10c Ho T.-L, Chen C.-K. Helv. Chim. Acta 2006; 89: 122
10d Flink H, Jokela R. Tetrahedron 2012; 68: 3811
10e Sebastiaan B, Lemmers JG. H, Floris L, Rutjes FP. J. T. Org. Biomol. Chem. 2012; 10: 945

11a Reddy CR, Dharmapuri G, Rao NN. Org. Lett. 2009; 11: 5730
11b Reddy CR, Latha B. Tetrahedron: Asymmetry 2011; 22: 1849
11c Reddy CR, Latha B, Rao NN. Tetrahedron 2012; 68: 145
11d Reddy CR, Dilipkumar U, Reddy MD, Rao NN. Org. Biomol. Chem. 2013; 11: 3355
11e Reddy CR, Latha B, Warudikar K, Singarapu K. Org. Biomol. Chem. 2016; 14: 251

Selected references for the synthesis of indolo[2,3-a]quinolizidines:

12a Gobé V, Dousset M, Retailleau P, Gandon V, Guinchard X. J. Org. Chem. 2018; 83: 898
12b Lalonde MP, McGowan MA, Rajapaksa NS, Jacobsen EN. J. Am. Chem. Soc. 2013; 135: 1891
12c Gobé V, Guinchard X. Chem. Eur. J. 2015; 21: 8511
12d Gobé V, Guinchard X. Org. Lett. 2014; 16: 1924
12e Yu T, Han-Lin L, Hua L, Sun X-W, Yang X-D, Dongbc H-Q, Lin G-Q. Chem. Commun. 2014; 50: 10027
12f Suryavanshi PA, Sridharan V, Menéndez JC. Chem. Eur. J. 2013; 19: 13207
12g Zhu H.-L, Ling J.-B, Xu P.-F. J. Org. Chem. 2012; 77: 7737
12h Wu X.-Y, Dai X.-Y, Fang H.-H, Nie L.-L, Chen J, Cao W.-G, Zhao G. Chem. Eur. J. 2011; 17: 10510
12i Stockigt J, Antonchick AP, Wu FR, Waldmann H. Angew. Chem. Int. Ed. 2011; 50: 8538
12j Zhang W, Bah J, Wohlfarth A, Franzén J. Chem. Eur. J. 2011; 17: 13814
12k Rueping M, Volla CM. R, Bolte M, Raabe G. Adv. Synth. Catal. 2011; 353: 2853
12l Wu X.-Y, Dai X.-Y, Nie L.-L, Fang H.-H, Chen J, Ren Z.-J, Cao W.-G, Zhao G. Chem. Commun. 2010; 46: 2733
12m Fang H.-H, Wu X.-Y, Nie L.-L, Dai X.-Y, Chen J, Cao W.-G, Zhao G. Org. Lett. 2010; 12: 5366
12n Franzén J, Fisher A. Angew. Chem. Int. Ed. 2009; 48: 787

13a Wubin Z, Jingya L, Dapeng Z, Wu WY, Yangjie W. J. Org. Chem. 2017; 82: 12286
13b Sádaba D, Delso I, Tejero T, Merino P. Tetrahedron Lett. 2011; 52: 5976

14 For chemoselective reduction of enones: Hays D, Scholl M, Fu C-G. J. Org. Chem. 1996; 61: 6751 ; and references cited therein

Conditions attempted for intramolecular C3 acylation:

15a MeSO₃H, 70 °C, 4 h – inseparable mixture of polar compounds.
15b pTSA, toluene, reflux, 12 h – no product.
15c PPA, 70 °C, 12 h – no reaction progress.

Zusatzmaterial

Supporting Information

Facile Strategy to Access the Indolo[2,3-a]quinolizidine Framework: Synthetic Study on Tangutorine[1]

Facile Strategy to Access the Indolo[2,3-a]quinolizidine Framework: Synthetic Study on Tangutorine^[1]