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-00000083.xml
Synlett 2015; 26(05): 572-579
DOI: 10.1055/s-0034-1379964
DOI: 10.1055/s-0034-1379964
synpacts
Strategies for the Synthesis of Antifeedant Leucosceptroid Natural Products
Further Information
Publication History
Received: 30 October 2014
Accepted after revision: 09 December 2014
Publication Date:
12 January 2015 (online)
Abstract
The evolving pathogen resistance in agricultural pests requires the development of novel chemical agents to maintain efficient pest control. Biological screening of natural products isolated from Leucosceptrum canum Smith led to the discovery of active antifeedant sesterterpenoids. This article highlights recent progress towards the synthesis of these natural products.
1 Introduction
2 Synthesis of the Leucosceptroid Core Structure
3 Total Synthesis of Leucosceptroid B
4 Towards the Collective Synthesis of Leucosceptroid Natural Products
5 Total Synthesis of Leucosceptroids A and B
6 Summary
-
References and Notes
- 1 For a recent review of natural product syntheses involving the preparation of gram-scale quantities of a target compound or intermediate, see: Kuttruff CA, Eastgate MD, Baran PS. Nat. Prod. Rep. 2014; 31: 419
- 2 Wender PA. Chem. Rev. 1996; 96: 1
-
3 Trost BM. Science 1991; 254: 1471
- 4 Young IS, Baran PS. Nat. Chem. 2009; 1: 193
- 5 Wu K.-M, Lu Y.-H, Feng H.-Q, Jiang Y.-Y, Zhao J.-Z. Science 2008; 321: 1676
- 6 Bhonwong A, Stout MJ, Attajarusit J, Tantasawa P. J. Chem. Ecol. 2009; 35: 28
- 7a Sandoval-Mojica AF, Capinera JL. Pest Manage. Sci. 2011; 67: 860
- 7b Koul O. Crit. Rev. Plant Sci. 2008; 27: 1
- 7c Ballesta-Acosta MC, Pascual-Villalobos MJ, Rodríguez B. Span. J. Agric. Res. 2008; 6
- 7d Isman MB. Annu. Rev. Entomol. 2006; 51: 45
- 8a Luo S.-H, Luo Q, Niu X.-M, Xie M.-J, Zhao X, Schneider B, Gershenzon J, Li S.-H. Angew. Chem. Int. Ed. 2010; 49: 4471
- 8b Luo S.-H, Weng L.-H, Xie M.-J, Li X.-N, Hua J, Zhao X, Li S.-H. Org. Lett. 2011; 13: 1864
- 8c Luo S.-H, Hua J, Niu X.-M, Liu Y, Li C.-H, Zhou Y.-Y, Jing S.-X, Zhao X, Li S.-H. Phytochemistry 2013; 86: 29
- 8d Luo S.-H, Hua J, Li C.-H, Liu Y, Li X.-N, Zhao X, Li S.-H. Tetrahedron Lett. 2013; 54: 235
- 9 Luo S.-H, Hua J, Li C.-H, Jing S.-X, Liu Y, Li X.-N, Zhao X, Li S.-H. Org. Lett. 2012; 14: 5768
- 10 Luo S.-H, Hugelshofer CL, Hua J, Jing S.-X, Li C.-H, Liu Y, Li X.-N, Zhao X, Magauer T, Li S.-H. Org. Lett. 2014; 16: 6416
- 11 Hog DT, Webster R, Trauner D. Nat. Prod. Rep. 2012; 29: 752
- 12 Xie J, Ma Y, Horne DA. J. Org. Chem. 2011; 76: 6169
- 13 Huang X, Song L, Xu J, Zhu G, Liu B. Angew. Chem. Int. Ed. 2013; 52: 952
- 14 Hugelshofer CL, Magauer T. Angew. Chem. Int. Ed. 2014; 53: 11351
- 15 Guo S, Liu J, Ma D. Angew. Chem. Int. Ed. 2014; 53 in press; DOI: 10.1002/anie.201410134
- 16 Cheng H, Stark CB. W. Angew. Chem. Int. Ed. 2010; 49: 1587
- 17 Esteban J, Costa AM, Gomez A, Vilarrasa J. Org. Lett. 2008; 10: 65
- 18 Brown HC, Jadhav PK, Bhat KS. J. Am. Chem. Soc. 1988; 110: 1535
- 19 Corey EJ, Guzman-Perez A, Noe MC. J. Am. Chem. Soc. 1995; 117: 10805
- 20 Mal D, Pahari P. Chem. Rev. 2007; 107: 1892
- 21 Our synthetic route for the synthesis of leucosceptroid natural products proceeding via dilactone 33 was developed following a first-generation approach. Details of our initial efforts, which ultimately proved unsuccessful, will be reported in due course.