Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Letter Article

Total Synthesis of Xestodecalactone C via Sharpless Epoxidation and Friedal-Crafts Acylation

Author(s): Chithaluri Sudhakar*, Kottolla Sai Prasad and Batharaju Ramesh

Volume 20, Issue 11, 2023

Published on: 07 July, 2023

Page: [1010 - 1015] Pages: 6

DOI: 10.2174/1570178620666230522115248

Price: $65

Abstract

Marine-derived macrolides that occur naturally exhibit a range of biological properties, including antibacterial and antifungal activity.

Sharpless epoxidation and intramolecular acylation via the Friedel-Crafts method for the macrolide ring formation was used as the main steps in the regioselective construction of naturally existing xestodecalactone C, which was started from chiral propylene oxide.

The isolated yellow coloured final product had a 91% yield, and FT-IR, Mass, 1H-NMR, and 13C NMR were used to characterise each product. As a result, chiral propylene oxide was used as the starting material for the regioselective total synthesis of the naturally occurring xestrodecalactone C, with the main stages being intramolecular Friedel-Crafts acylation for macrolide ring formation and Sharpless epoxidation. The synthesis of numerous xestrodecalactone C analogues relevant for bioevaluation can be done quickly and easily using this synthetic approach.

« Previous Next »
Graphical Abstract

[1]
Evidente, A. Nat. Prod. Rep., 2022, 39(8), 1591-1621.
[http://dx.doi.org/10.1039/D2NP00025C] [PMID: 35723218]
[2]
Xu, J.; Jiang, C.; Zhang, Z.; Ma, W.; Guo, Y. Acta Pharmacol. Sin., 2014, 35(3), 316-330.
[http://dx.doi.org/10.1038/aps.2013.155] [PMID: 24464049]
[3]
Bernan, V.S.; Greenstein, M.; Maiese, W.M. Adv. Appl. Microbiol., 1997, 43, 57-90.
[http://dx.doi.org/10.1016/S0065-2164(08)70223-5] [PMID: 9097412]
[4]
Jensen, P.R.; Fenical, W. Annu. Rev. Microbiol., 1994, 48(1), 559-584.
[http://dx.doi.org/10.1146/annurev.mi.48.100194.003015] [PMID: 7826019]
[5]
Sponga, F.; Cavaletti, L.; Lazzarini, A.; Borghi, A.; Ciciliato, I.; Losi, D.; Marinelli, F. J. Biotechnol., 1999, 70(1-3), 65-69.
[http://dx.doi.org/10.1016/S0168-1656(99)00059-0]
[6]
Edrada, R.A.; Heubes, M.; Brauers, G.; Wray, V.; Berg, A.; Gräfe, U.; Wohlfarth, M.; Mühlbacher, J.; Schaumann, K.; Sudarsono, S.; Bringmann, G.; Proksch, P. J. Nat. Prod., 2002, 65(11), 1598-1604.
[http://dx.doi.org/10.1021/np020085c] [PMID: 12444683]
[7]
Reddy, G.N.; Mura Reddy, G.; Sridhar, G.; Prasad, K.R.S. Nat. Prod. Res., 2022, 36(21), 5416-5422.
[http://dx.doi.org/10.1080/14786419.2021.1941948] [PMID: 34157905]
[8]
Yoshino, T.; Ng, F.; Danishefsky, S.J. J. Am. Chem. Soc., 2006, 128(43), 14185-14191.
[http://dx.doi.org/10.1021/ja064270e] [PMID: 17061903]
[9]
Liang, Q.; Zhang, J.; Quan, W.; Sun, Y.; She, X.; Pan, X. J. Org. Chem., 2007, 72(7), 2694-2697.
[http://dx.doi.org/10.1021/jo070159v] [PMID: 17346089]
[10]
Yadav, J.S.; Thrimurtulu, N.; Uma Gayathri, K.; Subba Reddy, B.V.; Prasad, A.R. Tetrahedron Lett., 2008, 49(47), 6617-6620.
[http://dx.doi.org/10.1016/j.tetlet.2008.08.096]
[11]
Yadav, J.; Gopala Rao, Y.; Ravindar, K.; Subba Reddy, B.; Narsaiah, A. Synthesis, 2009, 2009(18), 3157-3161.
[http://dx.doi.org/10.1055/s-0029-1216938]
[12]
Novikov, A.S.; Kuznetsov, M.L.; Rocha, B.G.M.; Pombeiro, A.J.L.; Shul’pin, G.B. Catal. Sci. Technol., 2016, 6(5), 1343-1356.
[http://dx.doi.org/10.1039/C5CY01367D]
[13]
Pfenninger, A. Synthesis, 1986, 1986(2), 89-116.
[http://dx.doi.org/10.1055/s-1986-31489]
[14]
Das, B.; Krishnaiah, M.; Sudhakar, C. Bioorg. Med. Chem. Lett., 2010, 20(7), 2303-2305.
[http://dx.doi.org/10.1016/j.bmcl.2010.01.162] [PMID: 20194022]
[15]
Sudhakar, C.; Reddy, P.R.; Kumar, C.G.; Sujitha, P.; Das, B. Eur. J. Org. Chem., 2012, 2012(6), 1253-1258.
[http://dx.doi.org/10.1002/ejoc.201101601]
[16]
Das, B.; Srinivas, Y.; Sudhakar, C.; Raghavendar Reddy, P. Helv. Chim. Acta, 2011, 94(7), 1290-1295.
[http://dx.doi.org/10.1002/hlca.201000396]
[17]
Sudhakar, C.; Reddy, P.R.; Raju, T.V.; Das, B. Tetrahedron Lett., 2012, 53(30), 3850-3852.
[http://dx.doi.org/10.1016/j.tetlet.2012.05.032]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy