European Journal of Chemistry 2015, 6(1), 93-97 | doi: https://doi.org/10.5155/eurjchem.6.1.93-97.1150 | Get rights and content

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Stereoselective total synthesis of pectinolide H and 4'-epi-pectinolide H


Ramesh Perla (1) , Nitin Wasantrao Fadnavis (2,*)

(1) Natural Products Chemistry Division, Indian Institute of Chemical Technology, Habsiguda, Hyderabad-500007, India
(2) Natural Products Chemistry Division, Indian Institute of Chemical Technology, Habsiguda, Hyderabad-500007, India
(*) Corresponding Author

Received: 11 Sep 2014 | Revised: 13 Oct 2014 | Accepted: 18 Oct 2014 | Published: 31 Mar 2015 | Issue Date: March 2015

Abstract


The total synthesis of pectinolide H and 4'-epi-pectinolide H was accomplished with 27% yield in nine steps from inexpensive and commercially available compound, (+)-diethyl tartrate ((+)DET)) by employing swern oxidation, Wittig olefination, Grignard and lactonization reactions.


Keywords


Reduction; Pectinolide H; Lactonization; Swern oxidation; Wittig olefination; Grignard reaction

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DOI: 10.5155/eurjchem.6.1.93-97.1150

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Funding information


University Grants Commission for grant of Senior Research Fellowship to PR and Council of Scientific and Industrial Research, New Delhi for financial assistance under XII 5 year plan CSC0108-ORIGIN

Citations

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[1]. Ramesh Saudagar Ghogare, Sachin Bibishan Wadavrao, Akkirala Venkat Narsaiah
Stereoselective Total Synthesis of Pectinolides A, C, and H
Helvetica Chimica Acta  99(4), 247, 2016
DOI: 10.1002/hlca.201500110
/

References


[1]. Fragoso-Serrano, M.; Gibbons, S.; Perda-Miranda, R. Planta Med. 2005, 71, 278-280.
http://dx.doi.org/10.1055/s-2005-837831

[2]. Hentzer, M.; Eberl, L.; Nielsen, J.; Giviskov, M. Biodrugs 2003, 17, 241-250.
http://dx.doi.org/10.2165/00063030-200317040-00003

[3]. Hjelmgaard, T.; Persson, T.; Rasmussen, T. B.; Givskov, M.; Nielsen. J. Bioorg. Med. Chem. 2003, 11, 3261-3271.
http://dx.doi.org/10.1016/S0968-0896(03)00295-5

[4]. Fusetani, N. Nat. Prod. Rep. 2004, 21, 94-104.
http://dx.doi.org/10.1039/b302231p

[5]. Cateni, F.; Zillic, J.; Zacchigna, M.; Bonivento, P.; Frausin, F.; Carcia, V. Eur. J. Med. Chem. 2006, 41, 192-200.
http://dx.doi.org/10.1016/j.ejmech.2005.10.009

[6]. Marcos, I. S.; Escola, M. A.; Moro, R. F.; Basabe, P.; Diez, D.; Sanz, F.; Mollinedo, F.; Dela Iglesia-Vicente, J.; Sierrac, B. G.; Urones, J. G. Bioorg. Med. Chem. 2007, 15, 5719-5737.
http://dx.doi.org/10.1016/j.bmc.2007.06.007

[7]. Takahashi, M.; Dodo, K.; Sugimoto, Y.; Aoyagi, Y.; Yamada, Y.; Hashimoto, Y.; Shirai, R. Bioorg. Med. Chem. Lett. 2000, 10, 2571-2574.
http://dx.doi.org/10.1016/S0960-894X(00)00527-8

[8]. Brohm, D.; Philippe, N.; Metzger, S.; Bhargava, A.; Muller, O.; Lieb, F.; Waldmann, H. J. Am. Chem. Soc. 2002, 124, 13171-13178.
http://dx.doi.org/10.1021/ja027609f

[9]. Li, D. H.; Zhu, T. J.; Liu, H. B.; Fang, C. Y.; Gu, Q. Q.; Zhu, W. M. Arch. Pharm. Res. 2006, 29, 624-626.
http://dx.doi.org/10.1007/BF02968245

[10]. Ma, S.; Shi, Z.; Yu, Z. Tetrahedron 1999, 55, 12137-12148.
http://dx.doi.org/10.1016/S0040-4020(99)00726-7

[11]. Ramesh, D.; Shekhar, V.; Chantibabu, D.; Rajaram, S.; Ramulu, U.; Venkateswarlu Y. Tetrahedron Lett. 2012, 53, 1258-1260.
http://dx.doi.org/10.1016/j.tetlet.2011.12.122

[12]. Sabitha, G.; Anki Reddy, P.; Kishore Das, S.; Yadav, J. S. Synthesis 2013, 45, 651-654.
http://dx.doi.org/10.1055/s-0032-1318000

[13]. Subhash, P. C.; Kishor, R. H.; Nilesh B. D.; Uttam, R. K. Tetrahedron Asymm. 2011, 22, 587-590.
http://dx.doi.org/10.1016/j.tetasy.2011.02.023

[14]. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408.
http://dx.doi.org/10.1016/S0040-4039(00)85909-2

[15]. Krishna, P. R.; Reddy, P. S. Tetrahedron 2007, 63, 3995-3999.
http://dx.doi.org/10.1016/j.tet.2007.03.011


How to cite


Perla, R.; Fadnavis, N. Eur. J. Chem. 2015, 6(1), 93-97. doi:10.5155/eurjchem.6.1.93-97.1150
Perla, R.; Fadnavis, N. Stereoselective total synthesis of pectinolide H and 4'-epi-pectinolide H. Eur. J. Chem. 2015, 6(1), 93-97. doi:10.5155/eurjchem.6.1.93-97.1150
Perla, R., & Fadnavis, N. (2015). Stereoselective total synthesis of pectinolide H and 4'-epi-pectinolide H. European Journal of Chemistry, 6(1), 93-97. doi:10.5155/eurjchem.6.1.93-97.1150
Perla, Ramesh, & Nitin Wasantrao Fadnavis. "Stereoselective total synthesis of pectinolide H and 4'-epi-pectinolide H." European Journal of Chemistry [Online], 6.1 (2015): 93-97. Web. 2 Mar. 2021
Perla, Ramesh, AND Fadnavis, Nitin. "Stereoselective total synthesis of pectinolide H and 4'-epi-pectinolide H" European Journal of Chemistry [Online], Volume 6 Number 1 (31 March 2015)

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