Divergent Synthesis and Biological Evaluation of 2,6-Disubstituted Tetrahydropyran-Containing Natural Products: Parvistone E, Goniothalesdiol A, 6-epi-Goniothalesdiol A, and 8-epi-9-Deoxygoniopypyrone

Ziyang Zhao; Ruiying Pan; Qingwei Lv; Xinni Xie; Jun Liu; Yuguo Du

doi:10.1055/a-2149-4214

Synthesis, Table of Contents

Synthesis 2023; 55(23): 3961-3968
DOI: 10.1055/a-2149-4214

paper

Divergent Synthesis and Biological Evaluation of 2,6-Disubstituted Tetrahydropyran-Containing Natural Products: Parvistone E, Goniothalesdiol A, 6-epi-Goniothalesdiol A, and 8-epi-9-Deoxygoniopypyrone

Authors

Ziyang Zhao

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China
Ruiying Pan

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China

^bSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
Qingwei Lv

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China
Xinni Xie∗

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China

^bSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
Jun Liu ∗

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China

^bSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China

^cBinzhou Institute of Technology, Weiqiao-UCAS Science and Technology Park, Binzhou 256606, Shandong Province, P. R. of China
Yuguo Du

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China

^bSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China

^cBinzhou Institute of Technology, Weiqiao-UCAS Science and Technology Park, Binzhou 256606, Shandong Province, P. R. of China

Abstract

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Abstract

The concise and efficient synthesis of (+)-goniothalesdiol A and (–)-parvistone E (leiocarpin A), as well as the first total syntheses of (–)-6-epi-goniothalesdiol A and (–)-8-epi-9-deoxygoniopypyrone acetate, have been achieved in four or five longest linear steps based on the chiron approach. The potential biological activities of four 2,6-disubstituted tetrahydropyran-containing natural products were explored based on a panel of human cancer cell lines, BV-2 microglia and 3T3-L1 preadipocytes. Our results indicate that these four natural products display significant adipogenic activity in 3T3-L1 preadipocytes, but do not have clear effects on cancer cell proliferation or LPS stimulated microglia activation.

Key words

goniothalesdiol A - parvistone E (leiocarpin A) - 6-epi-goniothalesdiol A - 8-epi-9-deoxygoniopypyrone acetate - total synthesis - adipogenesis

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References

References

1a For a review on chemistry, biogenesis, and biological activities of styryl lactones from Goniothalamus species, see: Blazquez MA, Bermejo A, Zafra-Polo MC, Cortes D. Phytochem. Anal. 1999; 10: 161
1b de Fatima A, Modolo LV, Conegero LS, Pilli RA, Ferreira CV, Kohn LK, de Carvalho JE. Curr. Med. Chem. 2006; 13: 3371
1c Mereyala HB, Joe M. Curr. Med. Chem.: Anti-Cancer Agents 2001; 1: 293
1d Seyed MA, Jantan I, Bukhari SN. A. BioMed Res. Int. 2014; 536508
1e Choo C.-Y, Abdullah N, Diederich M. Phytochem. Rev. 2014; 13: 835

2 Lan Y.-H, Chang F.-R, Yang Y.-L, Wu Y.-C. Chem. Pharm. Bull. 2006; 54: 1040
3 Suchaichit N, Kanokmedhakul K, Panthama N, Poopasit K, Moosophon P, Kanokmedhakul S. Fitoterapia 2015; 103: 206
4 Mu Q, Tang W, Li C, Lu Y, Sun H, Zheng X, Wu N, Lou B, Xu B. Heterocycles 1999; 12: 2969
5 Tai BH, Huyen VT, Huong TT, Nhiem NX, Choi EM, Kim JA, Long PQ, Cuong NM, Kim YH. Chem. Pharm. Bull. 2010; 58: 521
6 Liou J.-R, Wu T.-Y, Thang TD, Hwang T.-L, Wu C.-C, Cheng Y.-B, Chiang MY, Lan Y.-H, El-Shazly M, Wu S.-L, Beerhues L, Yuan S.-S, Hou M.-F, Chen S.-L, Chang F.-R, Wu Y.-C. J. Nat. Prod. 2014; 77: 2626

7a Prawat U, Chaimanee S, Butsuri A, Salae AB, Tuntiwachwuttikul P. Phytochem. Lett. 2012; 5: 529
7b Due to differences in numbering systems, compound 4 is sometimes named iso-5-deoxygoniopypyrone, see: Goh SH, Ee GC. L, Chuah CH, Wei C. Aust. J. Chem. 1995; 48: 199

For reviews on syntheses of styryl lactones, see:

8a Mondon M, Gesson J.-P. Curr. Org. Synth. 2006; 3: 41
8b Zhao G, Wu B, Wu XY, Zhang YZ. Mini-Rev. Org. Chem. 2005; 2: 333
8c Pilli RA, de Toledo I, Meirelles MA, Grigolo TA. Curr. Med. Chem. 2019; 26: 7372

For the total syntheses of goniothalesdiol A, see:

9a Yadav JS, Rami Reddy N, Harikrishna V, Subba Reddy BV. Tetrahedron Lett. 2009; 50: 1318
9b Venkataiah M, Somaiah P, Reddipalli G, Fadnavis NW. Tetrahedron: Asymmetry 2009; 20: 2230
9c Yadav JS, Rao RN, Somaiah R, Harikrishna V, Subba Reddy BV. Helv. Chim. Acta 2010; 93: 1362
9d Li J, Zheng H, Su Y, Xie X, She X. Synlett 2010; 2283
9e Sabitha G, Reddy TR, Yadav JS. Tetrahedron Lett. 2011; 52: 6550
9f Pallavi T, Kumaraswamy B, Raji RG, Rakeshwar B, Khagga M. Tetrahedron: Asymmetry 2012; 23: 659
9g Ramesh P, Reddy YN. Tetrahedron Lett. 2017; 58: 1037
9h Zeng PL, Zhou JH, Yang X, Wang D, Dong ZB. Lett. Org. Chem. 2022; 19: 1145

For recent total synthesis of leiocarpin A, see:

9i Surivet JP, Vatele JM. Tetrahedron 1999; 55: 13011
9j Chen J, Lin GQ, Liu HQ. Tetrahedron Lett. 2004; 45: 8111
9k Nagaiah K, Sreenu D, Purnima KV, Rao RS, Yadav JS. Synthesis 2009; 1386
9l Paioti PH. S, Coelho F. Tetrahedron Lett. 2011; 52: 6180
9m Meruva SB, Raghavendra RK, Mohammed A, Dahanukar VH, Kumar UK. S, Dubey PK. Synth. Commun. 2016; 46: 187
9n Li Z, Tong R. Synthesis 2016; 48: 1630
9o Ramesh P, Rao TP. J. Nat. Prod. 2016; 79: 2060

10a Liu J, Zhang X, Liu Y, Bi J, Du Y. Sci. China Chem. 2013; 56: 928
10b Hu C, Zhao Z, Nie P, Du Y, Feng F, Liu J. Tetrahedron 2022; 105: 132609

For selected reviews of O-Michael addition and the applications in natural product synthesis, see:

11a Nising CF, Brase S. Chem. Soc. Rev. 2008; 37: 1218
11b Nising CF, Brase S. Chem. Soc. Rev. 2012; 41: 988
11c Wang Y, Du D. Org. Chem. Front. 2020; 7: 3266

12a Liu YX, Liu J, Zhao CF, Du YG. Org. Lett. 2021; 23: 3264
12b Liu Y, Zhao ZY, Hu C, Zhao CF, Liu J, Du YG. SynLett 2022; 33: 478
12c Zhao ZY, Lv QW, Geng JL, Liu Y, Hu C, Du YG, Liu J. Synthesis 2023; 55: 341

13 Chang C, Geng J, Liu Y, Du Y, Liu J, Dong Z. Synthesis 2020; 52: 1576

14a Bercier A, Plantier-Royon R, Portella C. Tetrahedron 2010; 66: 4109
14b Palmer AM, Jäger V. Eur. J. Org. Chem. 2001; 1293
14c Bernet B, Vasella A. Helv. Chim. Acta 1979; 62: 1990

15 The known allylic alcohol 6 was also prepared in 15% yield over six steps from d-ribonolactone, see: Robertson J, Unsworth WP, Lamont SG. Tetrahedron 2010; 66: 2363
16 Liu J, Liu Y, Zhang X, Zhang C, Gao Y, Wang L, Du Y. J. Org. Chem. 2012; 77: 9718
17 See the Supporting Information for detailed comparisons of the ¹H and ¹³C NMR spectra of natural and synthetic samples.
18 Lekphrom R, Kanokmedhakul S, Kanokmedhakul K. J. Ethnopharmacol. 2009; 125: 47
19 Yu C, Wen Q, Ren Q, Du Y, Xie X. Food Chem. Toxicol. 2021; 152: 112205

Supplementary Material

Supporting Information (PDF)