Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2021; 53(10): 1749-1759
DOI: 10.1055/s-0037-1610763
DOI: 10.1055/s-0037-1610763
feature
Pyrrolidine and Indolizidine Alkaloids from Chiral N-tert-Butanesulfinyl Imines Derived from 4-Halobutanal
For continuous financial support we thank the Spanish Ministerio de Economía y Competitividad (MINECO; projects CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P), Ministerio de Ciencia, Innovación y Universidades (RED2018-102387-T, PID2019-107268GB-100), FEDER, the Generalitat Valenciana (PROMETEOII/2014/017), and the University of Alicante (VIGROB-068).
Dedicated to Professor Joaquín Plumet on the occasion of his 75th birthday
Abstract
An efficient stereocontrolled preparation of 2-substituted pyrrolidines and 5-substituted indolizidin-7-ones, by using chiral N-tert-butanesulfinyl imines derived from 4-halobutanal as starting materials, is detailed. Addition of Grignard reagents and a decarboxylative Mannich reaction with β-keto acids involving these chiral imines proceeded with high diastereoselectivity. The synthesis of the pyrrolidinic alkaloids (–)-bgugaine, (+)-villatamine B, (–)-norhygrine, trans-dendrochrysanine, and (–)-ruspolinone demonstrated the utility of this methodology.
Key words
chiral sulfinyl imines - diastereoselective additions - decarboxylative Mannich reaction - bgugaine - villatamine - norhygrine - trans-dendrochrysanine - ruspolinoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610763.
- Supporting Information
Publication History
Received: 27 November 2020
Accepted after revision: 11 January 2021
Article published online:
10 February 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Chen Q, Li J, Yuan C. Synthesis 2008; 2986
- 1b Reddy LR, Gupta AP, Villhauer R, Liu Y. J. Org. Chem. 2012; 77: 1095
- 1c Ye J.-L, Zhang Y.-F, Liu Y, Zhang J.-Y, Ruan Y.-P, Huang P.-Q. Org. Chem. Front. 2015; 2: 697
- 1d Burtea A, Rychnovsky SD. Org. Lett. 2017; 19: 4195
- 1e Mulamreddy R, Prasad Atmuri ND, Lubell WD. J. Org. Chem. 2018; 83: 13580
- 2a Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M. Chem. Rev. 2008; 108: 3795
- 2b Redford JE, McDonald RI, Rigsby ML, Wiensch JD, Stahl SS. Org. Lett. 2012; 14: 1242
- 2c Chen C, Jin S, Zhang Z, Wei B, Wang H, Zhang K, Lv H, Dong X.-Q, Zhang X. J. Am. Chem. Soc. 2016; 138: 9017
- 2d Pérez SJ, Purino MA, Cruz DA, López-Soria JM, Carballo RM, Ramírez MA, Fernández I, Martín VS, Padrón JI. Chem. Eur. J. 2016; 22: 15529
- 2e Gao P, Sipos G, Foster D, Dorta R. ACS Catal. 2017; 7: 6060
- 3a Morton D, Stockman RA. Tetrahedron 2006; 62: 8869
- 3b Ferreira F, Botuha C, Chemla F, Pérez-Luna A. Chem. Soc. Rev. 2009; 38: 1162
- 3c Robak MT, Herbage MA, Ellman JA. Chem. Rev. 2010; 110: 3600
- 4a Sirvent JA, Foubelo F, Yus M. Chem. Commun. 2012; 48: 2543
- 4b Barros OS. R, Sirvent JA, Foubelo F, Yus M. Chem. Commun. 2014; 50: 6898
- 4c Sirvent JA, Foubelo F, Yus M. J. Org. Chem. 2014; 79: 1356
- 4d García-Muñoz MJ, Dema HK, Foubelo F, Yus M. Tetrahedron: Asymmetry 2015; 26: 362
- 4e García-Muñoz MJ, Foubelo F, Yus M. J. Org. Chem. 2016; 81: 10214
- 4f Maciá E, Foubelo F, Yus M. Tetrahedron: Asymmetry 2017; 28: 1407
- 4g Maciá E, Foubelo F, Yus M. Heterocycles 2019; 99: 248
- 4h Sirvent A, García-Muñoz MJ, Yus M, Foubelo F. Eur. J. Org. Chem. 2020; 113
- 4i Hernández-Ibáñez S, Barros OS. R, Lahosa A, García-Muñoz MJ, Benlahrech M, Behloul C, Foubelo F, Yus M. Tetrahedron 2020; 76: 130842
- 5 Reddy LR, Prashad M. Chem. Commun. 2010; 46: 222
- 6a Leemans E, Mangelinckx S, De Kimpe N. Chem. Commun. 2010; 48: 3122
- 6b Reddy LR, Das SG, Liu Y, Prashad M. J. Org. Chem. 2010; 75: 2236
- 6c Pablo O, Guijarro D, Yus M. J. Org. Chem. 2013; 78: 9181
- 7a Liu G, Cogan DA, Ellman JA. J. Am. Chem. Soc. 1997; 119: 9913
- 7b Cogan DA, Liu G, Ellman J. Tetrahedron 1999; 55: 8883
- 8a Sirvent JA, Foubelo F, Yus M. Heterocycles 2014; 88: 1163
- 8b Sirvent A, Foubelo F. Lett. Org. Chem. 2018; 15: 345
- 9 Chinchilla R, Foubelo F, Nájera C, Yus M. Tetrahedron: Asymmetry 1995; 6: 1877
- 10 Majik MS. Lett. Org. Chem. 2017; 14: 147
- 11 Melhaoui A, Jossang A, Bodo B. Nat. Prod. Lett. 1993; 2: 237
- 12 Melhaoui A, Belouali H. J. Ethnopharmacol. 1998; 62: 67
- 13 Davies SG, Fletcher AM, Roberts PM, Thomson JE, Zimmer D. Org. Lett. 2017; 19: 1638
- 14 For a synthesis of (+)-villatamine B, see: Hu L, Zhang L, Zhai H. J. Org. Chem. 2009; 74: 7552
- 15 Kubanek J, Williams DE, de Silva ED, Allen T, Andersen RJ. Tetrahedron Lett. 1995; 36: 6189
- 16 Lahosa A, Soler T, Arrieta A, Cossio FP, Foubelo F, Yus M. J. Org. Chem. 2017; 82: 7481
- 17 Yang L, Zhang C, Yang H, Zhang M, Wang Z, Xu L. Heterocycles 2005; 65: 633
- 18 Roessler F, Ganzinger D, Johne S, Schopp E, Hesse M. Helv. Chim. Acta 1978; 61: 1200
- 19 Jones K, Woo K.-C. Tetrahedron 1991; 47: 7179
- 20 Lahosa A, Yus M, Foubelo F. J. Org. Chem. 2019; 84: 7331
- 21 Pilli RA, Dias LC, Maldaner AO. J. Org. Chem. 1995; 60: 717
- 22 For a synthesis of 20b, see: Chiou W.-H. Chen H.-Y. 2017; 7: 684
- 23 Reddy AA, Prasad KR. J. Org. Chem. 2018; 83: 10776
- 24 Jossang A, Melhaoui A, Bodo B. Heterocycles 1996; 43: 755
- 25 Shu C, Liu M.-Q, Wang S.-S, Li L, Ye L.-W. J. Org. Chem. 2013; 78: 3292
- 26 Konno H, Kusumoto S, Kanai S, Yamahana Y, Nosaka K, Akaji K. Heterocycles 2006; 68: 2579
See, for instance:
For reviews, see:
See, for instance: