Subscribe to RSS
DOI: 10.1055/a-1856-7334
Syntheses of Aristotelia Alkaloids: Reflections in the Chiral Pool
We gratefully acknowledge startup funds provided by the University of Illinois at Chicago that provided funding for this work. Additional support was provided to A.P.R. by the National Institutes of Health, UIC Clinical and Translational Science Scholars Program (KL2TR0020002).
Abstract
The Aristotelia alkaloids are a family of monoterpene indole alkaloids possessing a characteristic azabicyclononane scaffold, which has been assembled by several synthetic methods. Herein we review those approaches that have adopted a biomimetic approach to unite heterocyclic synthons with chiral-pool monoterpenes. Throughout this discussion, the tendency of monoterpenes like α-pinene and limonene to undergo racemization is highlighted, revealing the challenges in developing stereospecific syntheses of these alkaloids. Finally, we provide a brief discussion of how these synthetic efforts have enabled the structural confirmation and elucidation of the Aristotelia alkaloids’ absolute configurations, including our own recent efforts to employ bioactivity data to deduce the naturally occurring configuration of the quinoline alkaloid aristoquinoline.
1 Introduction
2 Mercury-Mediated Ritter-Like Reactions
3 Brønsted Acid Mediated Ritter-Like Reactions
4 Synthesis of Aristoquinoline: Ritter-Like Reaction Approach
5 Aza-Prins-Type Reaction in the Synthesis of Aristotelia Alkaloids
6 Determination of Naturally Occurring Absolute Stereochemistry
7 Conclusions
Publication History
Received: 05 May 2022
Accepted after revision: 19 May 2022
Accepted Manuscript online:
19 May 2022
Article published online:
15 June 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Michel S, Tillequin F. Biomimetic Synthesis of Alkaloids Derived from Tryptophan: Indolemonoterpene Alkaloids. In Biomimetic Organic Synthesis; 2011. Ed.; 91-116.
- 2 O'Connor SE, Maresh JJ. Nat. Prod. Rep. 2006; 23 532
- 3 Bick IR. C, Hai MA, Preston NW. Heterocycles 1979; 12: 1563
- 4 Ralph I, Bick C, Hai MA. Aristotelia Alkaloids . In The Alkaloids: Chemistry and Pharmacology, Vol. 24, Chap. 3. Brossi A. Academic Press; London: 1985: 113-151
- 5 Stoermer D, Heathcock CH. J. Org. Chem. 1993; 58: 564
- 6 Gribble GW, Barden TC. J. Org. Chem. 1985; 50: 5900
- 7 Washburn DG, Heidebrecht RW, Martin SF. Org. Lett. 2003; 5: 3523
- 8 Delpech B, Khuong Huu Q. J. Org. Chem. 1978; 43: 4898
- 9 Mirand C, Massiot G, Levy J. J. Org. Chem. 1982; 47: 4169
- 10 Stevens RV, Kenney PM. J. Chem. Soc., Chem. Commun. 1983; 384
- 11 Caram J, Martins ME, Marschoff CM, Cafferata LF, Gros E. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1984; 39: 972
- 12 Rodriguez JB, Gros EG, Caram JA, Marschoff CM. Tetrahedron Lett. 1995; 36: 7825
- 13 Samaniego WN, Baldessari A, Ponce MA, Rodriguez JB, Gros EG, Caram JA, Marschoff CM. Tetrahedron Lett. 1994; 35: 6967
- 14 Argade MD, Straub CJ, Rusali LE, Santarsiero BD, Riley AP. Org. Lett. 2021; 23: 7693
- 15 Gujarati PD, Reber KP. Synthesis 2022; 54: 1404
- 16 Jiang D, He T, Ma L, Wang Z. RSC Adv. 2014; 4: 64936
- 17 Mohammadi Ziarani G, Soltani Hasankiadeh F, Mohajer F. ChemistrySelect 2020; 5: 14349
- 18 Chen M.-E, Chen X.-W, Hu Y.-H, Ye R, Lv J.-W, Li B, Zhang F.-M. Org. Chem. Front. 2021; 8 4623
- 19 Darbre T, Nossbaumer C, Borschberg HJ. Helv. Chim. Acta 1984; 67: 1040
- 20 Burkard S, Borschberg HJ. Helv. Chim. Acta 1989; 72: 254
- 21 Burkard S, Borschberg HJ. Helv. Chim. Acta 1991; 74: 275
- 22 Güller R, Dobler M, Borschberg HJ. Helv. Chim. Acta 1991; 74: 1636
- 23 Beerli R, Borschberg HJ. Helv. Chim. Acta 1991; 74: 110
- 24 Dobler M, Beerli R, Weissmahr WK, Borschberg H.-J. Tetrahedron: Asymmetry 1992; 3: 1411
- 25 Stahl R, Galli R, Güller R, Borschberg HJ. Helv. Chim. Acta 1994; 77: 2125
- 26 Dryzhakov M, Hellal M, Wolf E, Falk FC, Moran J. J. Am. Chem. Soc. 2015; 137: 9555
- 27 Yuasa Y, Yuasa Y. Org. Process Res. Dev. 2006; 10: 1231
- 28 Arias HR, Ortells MO, Feuerbach D, Burgos V, Paz C. J. Nat. Prod. 2019; 82: 1953
- 29 Anderson BF, Robertson GB, Avey HP, Donovan WF, Bick IR. C, Bremner JB, Finney AJ. T, Preston NW, Gallagher RT, Russell GB. J. Chem. Soc., Chem. Commun. 1975; 511
- 30 Battersby AR, Parry RJ. J. Chem. Soc., Chem. Commun. 1971; 31
- 31 Dineley KT, Pandya AA, Yakel JL. Trends Pharmacol. Sci. 2015; 36: 96