Synthesis of the Structure Proposed for Natural Meliloester

Lu Ding; Zhong-Han Li; Xiao-Wei Lu; Yikang Wu; Yan Li

doi:10.1055/s-0032-1316776

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(21): 3296-3300
DOI: 10.1055/s-0032-1316776

paper

Synthesis of the Structure Proposed for Natural Meliloester

Lu Ding

^aMinistry-of-Education Key Laboratory for Synthesis and Application of Organic Functional Molecules and School of Chemistry and Chemical Engineering, Hubei University, 11 Xueyuan Road, Wuhan 430062, P. R. of China

^bState Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: yikangwu@sioc.ac.cn

,

Zhong-Han Li

^bState Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: yikangwu@sioc.ac.cn

,

Xiao-Wei Lu

^bState Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: yikangwu@sioc.ac.cn

,

Yikang Wu*

^bState Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: yikangwu@sioc.ac.cn

,

Yan Li*

^aMinistry-of-Education Key Laboratory for Synthesis and Application of Organic Functional Molecules and School of Chemistry and Chemical Engineering, Hubei University, 11 Xueyuan Road, Wuhan 430062, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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.

Key words

esters - alcohols - natural products - aldol - phenols

Volltext

Referenzen

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

The structure 1 was previously mentioned in two patents, see:

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

Zusatzmaterial

Supporting Information