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 2012; 44(21): 3296-3300
DOI: 10.1055/s-0032-1316776
DOI: 10.1055/s-0032-1316776
paper
Synthesis of the Structure Proposed for Natural Meliloester
Further Information
Publication History
Received: 17 July 2012
Accepted after revision: 20 August 2012
Publication Date:
31 August 2012 (online)
Abstract
In an attempt to establish the absolute configuration of meliloester, a natural product isolated from Melilotus alba, the literature structure was synthesized in an enantiopure form. Unexpectedly, the 1H and 13C NMR data was completely incompatible with those reported for the natural product. The corresponding m-hydroxy isomer was also excluded as the structure for the natural product.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Kang SS. J. Nat. Prod. 1988; 51: 335
- 1b Nicollier GF, Thompson AC. J. Agric. Food Chem. 1982; 30: 760
- 1c Khodakov GV, Akimov YA, Shashkov AS, Kintya PK, Grishkovets VI. Chem. Nat. Compd. (Engl. Transl.) 1994; 30: 704
- 1d Miyase T, Ohtsubo A, Ueno A, Noro T, Kuroyanagi M, Fukushima S. Chem. Pharm. Bull. 1982; 30: 1986
- 1e Nicollier GF, Thompson AC. J. Nat. Prod. 1983; 46: 183
- 2a Khatoon R, Saba N, Zahoor A, Summer S, Ahmad VU. Nat. Prod. Commun. 2012; 7: 61
- 2b Rudolph T, Buchholz H. WO 2006111233, 2006
- 2c Rudolph T, Buchholz H. WO 2006111234, 2006
- 3 For a practical high-yielding route to such auxiliaries, see: Wu Y.-K, Shen X. Tetrahedron: Asymmetry 2000; 11: 4359
- 4 Crimmins MT, She J. Synlett 2004; 1371
- 5 Robins MJ, Wilson JS, Hansske F. J. Am. Chem. Soc. 1983; 105: 4059
- 6 Das SK, Panda G. Tetrahedron 2008; 64: 4162
- 7 Anderson MO, Moser J, Sherrill J, Guy RK. Synlett 2004; 2391
- 8 Welter TR. US 4720559, 1988
- 9a Shiina I, Kubota M, Ibuka R. Tetrahedron Lett. 2002; 43: 7535
- 9b Shiina I, Kubota M, Oshiumi H, Hashizume M. J. Org. Chem. 2004; 69: 1822
- 9c For an interesting case showing the advantage of MNBA, see: Wu Y.-K, Yang Y.-Q. J. Org. Chem. 2006; 71: 4296
- 10 El-Batta A, Jiang C, Zhao W, Anness R, Cooksy AL, Bergdahl M. J. Org. Chem. 2007; 72: 5244 ; but the synthesis was achieved via a Wittig reaction of the corresponding aldehyde under the conditions given in ref. 7 above
- 11 Hodgson DM, Kaka NS. Angew. Chem. Int. Ed. 2008; 47: 9958
- 12 Connor DT, Cetenko WA, Mullican MD, Sorenson RJ, Unangst PC, Weikort RJ, Adolphson RL, Kennedy JA, Thueson DO, Wright CD, Conroy MC. J. Med. Chem. 1992; 35: 958
The structure 1 was previously mentioned in two patents, see: