Total Synthesis of 5-Hydroxygoniothalamin

Santhosh Reddy Patpi; Guangyi Jin; Srinivas Kantevari

doi:10.1055/s-0037-1610997

Synthesis, Table of Contents

Synthesis 2019; 51(03): 780-786
DOI: 10.1055/s-0037-1610997

paper

Total Synthesis of 5-Hydroxygoniothalamin

Santhosh Reddy Patpi

^aDepartment of Crop Protection Chemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India

^bSchool of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518 060, Guangdong, P. R. of China

,

Guangyi Jin

^bSchool of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518 060, Guangdong, P. R. of China

^cCancer Research Center, Shenzhen University Health Science Center, Shenzhen 518 060, Guangdong, P. R. of China

,

Srinivas Kantevari*

^aDepartment of Crop Protection Chemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India

^dAcademy of Scientiﬁc and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India Email: kantevari@yahoo.com Email: ksriniva@iict.res.in

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Abstract

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Abstract

The total synthesis of 5-hydroxygoniothalamin is achieved from commercially available l-xylose. The α,β-unsaturated-δ-lactone core is constructed in very good yield by utilizing one-carbon and two-carbon cis-Wittig olefinations and δ-lactonization using Yamaguchi conditions. Subsequent Grubbs cross-metathesis followed by desilylation results in 5-hydroxygoniothalamin.

Key words

C1 Wittig reaction - C2 Wittig reaction - Yamaguchi reaction - cross-metathesis - 5-hydroxygoniothalamin

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References

References

1a Lahlou M. Exp. Opin. Drug Discovery 2007; 2: 697
1b Butler MS. J. Nat. Prod. 2004; 67: 2141
1c Lee K.-H. J. Nat. Prod. 2004; 67: 273
1d Clardy J. Walsh C. Nature 2004; 432: 829

2a Du L. Robles AJ. King JB. Powell DR. Miller AN. Mooberry SL. Cichewicz RH. Angew. Chem. Int. Ed. 2014; 53: 804
2b Bauer A. Brönstrup M. Nat. Prod. Rep. 2014; 31: 35
2c Hattum HV. Waldmann H. J. Am. Chem. Soc. 2014; 136: 11853
2d Brown DG. Lister T. May-Dracka TL. Bioorg. Med. Chem. Lett. 2014; 24: 413
2e Harvey AL. Edrada-Ebel R. Quinn RJ. Nat. Rev. Drug Discovery 2015; 14: 111
2f Lee ML. Schneider G. J. Comb. Chem. 2001; 3: 284

3a Yasui K. Tamura Y. Nakatani T. Kawada K. Ohtani M. J. Org. Chem. 1995; 60: 7554
3b Fang XP. Anderson JE. Chang CJ. McLaughlin JL. Fanwick PE. J. Nat. Prod. 1991; 54: 1034
3c Collins I. J. Chem. Soc., Perkin Trans. 1 1999; 1377

4a Yasui K. Tamura Y. Nakatani T. Kawada K. Ohtani M. J. Org. Chem. 1955; 60: 7567
4b Bermejo A. Blazqoz MA. Rao KS. Cortes D. Phytochem. Anal. 1999; 10: 127

5 Favier LS. Maria AO. M. Wendel GH. Borkowski EJ. Giordano OS. Pelzer L. Tonn CE. J. Ethnopharmacol. 2005; 100: 260
6 Rungeler P. Castro V. Mora G. Goren N. Vichnewski W. Pahl HL. Merfort I. Schmidt TJ. Bioorg. Med. Chem. 1999; 7: 2343

7a Goh SH. Ee GC. L. Chuah CH. Mak TC. W. Nat. Prod. Lett. 1995; 5: 255
7b de Fatima A. Modolo LV. Conegero LS. Pilli RA. Ferreira CV. Kohn LK. de Carvalho JE. Curr. Med. Chem. 2006; 13: 3371
7c Boucard V. Broustal G. Campagne JM. Eur. J. Org. Chem. 2007; 2: 225
7d Tuchindra P. Munyoo B. Pohmakotr M. Thinapong P. Sophasan S. Santisuk T. Reutrakul V. J. Nat. Prod. 2006; 69: 1728
7e Grove JF. J. Chem. Soc., Perkin Trans. 1 1985; 865
7f Prasad KR. Gutala P. Tetrahedron 2012; 68: 7489
7g Evans RH. Jr. Ellestad GA. Kunstman MP. Tetrahedron Lett. 1969; 22: 1791
7h Schlessinger RH. Gillman KW. Tetrahedron Lett. 1999; 40: 1257

8 Sam TW. Sew-Yeu C. Matsjeh S. Gan EK. Razak D. Mohamed AL. Tetrahedron Lett. 1987; 28: 2541

9a Harris JM. O’Doherty GA. Org. Lett. 2000; 2: 2983
9b Harris JM. O’Doherty GA. Tetrahedron 2001; 57: 5161

10a Pospísil J. Marko IE. Tetrahedron Lett. 2006; 47: 5933
10b Gupta P. Naidu SV. Kumar P. Tetrahedron Lett. 2004; 45: 849
10c Yadav JS. Kumar NN. Reddy MS. Prasad AR. Tetrahedron 2007; 63: 2689
10d de Fatima A. Kohn LK. Antonio MA. de Carvalho JE. Pilli RA. Bioorg. Med. Chem. 2004; 12: 5437
10e Lee H.-Y. Sampath V. Yoon Y. Synlett 2009; 249
10f Lin J. Qiu X.-L. Qing F.-L. Beilstein J. Org. Chem. 2010; 6: 1
10g Wach JY. Stephan G. Kutay U. Gademann K. Bioorg. Med. Chem. Lett. 2010; 20: 2843

11a Bouillon ME. Pyne SG. Tetrahedron Lett. 2014; 55: 475
11b Jiang B. Liu J.-F. Zhao S.-Y. J. Org. Chem. 2003; 68: 2376

12a Ogba OM. Warner NC. O’Leary DJ. Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510
12b Deraedt C. d’Halluin M. Astruc D. Eur. J. Inorg. Chem. 2013; 4881

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