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Letters in Organic Chemistry

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

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Short Communication

Concise Synthesis of Goniothalesdiol A

Author(s): Ping Li Zeng, Junhui Zhou, Xuechao Yang, Dong Wang* and Zhibing Dong

Volume 19, Issue 12, 2022

Published on: 14 June, 2022

Page: [1145 - 1148] Pages: 4

DOI: 10.2174/1570178619666220408121439

Price: $65

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Abstract

A concise and efficient synthesis of styryllactone derivative, goniothalesdiol A, has been achieved in the six longest linear steps with 17.7% overall yield. The key steps of our synthesis involved PdCl2-mediated Wacker-type oxidative cyclisation and one-pot tandem Wittig olefination- Michael addition.

Keywords: Total synthesis, goniothalesdiol A, styryllactone, L-erythrose, Wacker oxidation, Wittig olefination-Michael addition.

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[1]
Mereyala, H.B.; Joe, M. Curr. Med. Chem. Anticancer Agents, 2001, 1(3), 293-300.
[http://dx.doi.org/10.2174/1568011013354606] [PMID: 12678759]
[2]
Lan, Y.H.; Chang, F.R.; Yang, Y-L.; Wu, Y-C. Chem. Pharm. Bull. (Tokyo), 2006, 54(7), 1040-1043.
[http://dx.doi.org/10.1248/cpb.54.1040] [PMID: 16819228]
[3]
Yadav, J.S. Rami, Reddy, N.; Harikrishna, V.; Subba Reddy, B.V. Tetrahedron Lett., 2009, 50, 1318-1320.
[http://dx.doi.org/10.1016/j.tetlet.2009.01.050]
[4]
Yadav, J.S.; Nageshwar Rao, R.; Somaiah, R.; Harikrishna, V.; Subba Reddy, B.V. Helv. Chim. Acta, 2010, 93, 1362-1368.
[http://dx.doi.org/10.1002/hlca.200900342]
[5]
Venkataiah, M.; Somaiah, P.; Reddipalli, G.; Fadnavis, N.W. Tetrahedron Asymmetry, 2009, 20, 2230-2233.
[http://dx.doi.org/10.1016/j.tetasy.2009.08.005]
[6]
Li, J.; Zheng, H.; Su, Y.; Xie, X.; She, X. Synlett, 2010, 2283-2284.
[7]
Sabitha, G.; Rammohan Reddy, T.; Yadav, J.S. Tetrahedron Lett., 2011, 52, 6550-6553.
[http://dx.doi.org/10.1016/j.tetlet.2011.09.105]
[8]
Pallavi, T.; Kumaraswamy, B.; Raji, R.G.; Rakeshwar, B.; Khagga, M. Tetrahedron Asymmetry, 2012, 23, 659-661.
[http://dx.doi.org/10.1016/j.tetasy.2012.05.002]
[9]
Ramesh, P.; Reddy, Y.N. Tetrahedron Lett., 2017, 58, 1037-1039.
[http://dx.doi.org/10.1016/j.tetlet.2017.01.100]
[10]
Zeng, P.L.; Wang, D.; Zhou, J.H.; Dong, Z.B. J. Chem. Res., 2016, 40, 331-334.
[http://dx.doi.org/10.3184/174751916X14615896825798]
[11]
Mekki, B.; Singh, G.; Wightman, R.H. Tetrahedron Lett., 1991, 32, 5143-5146.
[http://dx.doi.org/10.1016/S0040-4039(00)93450-6]
[12]
Kim, J.H.; Kim, H.O.; Lee, K.M.; Chun, M.W.; Moon, H.R.; Jeong, L.S. Tetrahedron, 2006, 62, 6339-6342.
[http://dx.doi.org/10.1016/j.tet.2006.04.042]
[13]
Krishnudu, K.; Krishna, P.R.; Mereyala, H.B. Tetrahedron Lett., 1996, 37, 6007-6010.
[http://dx.doi.org/10.1016/0040-4039(96)01261-0]
[14]
Ohrui, H.; Jones, G.H.; Moffatt, J.G.; Maddox, M.L.; Christensen, A.T.; Byram, S.K. J. Am. Chem. Soc., 1975, 97, 4602-4613.
[http://dx.doi.org/10.1021/ja00849a023] [PMID: 1159224]

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