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  • P-ISSN 2233-4203
  • E-ISSN 2093-8950

Observations on Fragmentation Pathway of Farinomalein and its Isomers by Structural Investigation Using LC-MS/MS

Observations on Fragmentation Pathway of Farinomalein and its Isomers by Structural Investigation Using LC-MS/MS

Mass Spectrometry Letters / Mass Spectrometry Letters, (P)2233-4203; (E)2093-8950
2018, v.9 no.1, pp.37-40
https://doi.org/10.5478/MSL.2017.9.1.37
Narayan P. Firke (Affiliated to Shivaji University)
Anil G. Markandeya (Affiliated to Savitribai Phule Pune University)
Rajendra S. Konde Deshmukh (Affiliated to Savitribai Phule Pune University)
Shirish S. Pingale (Affiliated to Savitribai Phule Pune University)
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Abstract

Farinomalein is a maleimide-bearing compound well known for its anti-fungal activity. In the present study, synthesis of farinomalein is achieved via Stobbe condensation followed by Haval-Argade contrathermodynamic rearrangement. Kinetically driven Stobbe condensation followed by condensation with beta-alanine reveals formation of two isomers of farinomalein. This article describes application of LC-MS/MS in structure elucidation of farinomalein 1 and its isomers 2 and 3 encountered in its synthesis. The proposed distinct fragmentation pathway is supported by rational organic reaction mechanism. These fragmentation pathways are significant for analytical method development of farinomalein in near future. The structures of farinomalein 1 and its isomers 2 and 3 have been assigned undisputedly.

keywords
Maleimide, Stobbe condensation, Haval-Argade contrathermodynamic rearrangement, Isofarinomalein


참고문헌

1

Putri, S. P.. (2009). . J. Nat. Prod., 72, 1544-. http://dx.doi.org/10.1021/np9002806.

2

Miles, W. H.. (2010). . Tetrahedron Lett., 51, 1710-. http://dx.doi.org/10.1016/j.tetlet.2010.01.083.

3

Aiwale, S. T.. (2012). . Syn. Comm., 43, 1455-.

4

Lahore, S.. (2014). . Tetrahedron Lett., 55, 4196-4198. http://dx.doi.org/10.1016/j.tetlet.2014.05.023.

5

Rinehart, K. L.. (1965). . J. Am. Chem. Soc., 87, 4407-.

6

Biemann, K.. (2015). . Annu. Rev. Ana. Chem., 8, 1-. http://dx.doi.org/10.1146/annurev-anchem-071114-040110.

7

Kinghorn A.. (2015). Progress in the Chemistry of Organic Natural Products 100:Springer International Publishing.

8

Parichystal, J.. (2016). . Anal. Chem., 88, 10338-. http://dx.doi.org/10.1021/acs.analchem.6b02386.

9

Haval, K. P.. (2006). . Tetrahedron, 62, 3557-. http://dx.doi.org/10.1016/j.tet.2006.01.091.

10

Banerjee, S.. (2009). . Indian J. Chem., 48B, 882-.

11

Tanaka, K.. (2000). . Green Chem., 2, 303-. http://dx.doi.org/10.1039/b006565j.

12

White, J. D.. (1999). . J. Org. Chem., 64, 7871-. http://dx.doi.org/10.1021/jo990905z.

투고일Submission Date
2017-11-21
수정일Revised Date
2017-12-27
게재확정일Accepted Date
2018-01-10
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