O-Vinylphosphonylated Salicylaldehydes as Aldo-Vinyl Bifunctional Building Blocks for anti-3,4-Disubstituted Phosphadihydrocoumarins

Qinghe Wang; Dulin Kong; Tiao Huang; Mingshu Wu

doi:10.1055/s-0037-1611528

Synthesis, Table of Contents

Synthesis 2019; 51(15): 2923-2935
DOI: 10.1055/s-0037-1611528

paper

O-Vinylphosphonylated Salicylaldehydes as Aldo-Vinyl Bifunctional Building Blocks for anti-3,4-Disubstituted Phosphadihydrocoumarins

Authors

Qinghe Wang

^aKey Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China
Dulin Kong

^bSchool of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China Email: wmsh@hainnu.edu.cn
Tiao Huang

^aKey Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China
Mingshu Wu*

^aKey Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China

Abstract

All articles of this category

Abstract

An efficient synthetic strategy for anti-3,4-disubstituted phosphadihydrocoumarin compounds has been established by tandem aza-Michael–aldol-like annulations of tetrahydroisoquinolines with O-vinylphosphonylated salicylaldehydes as an aldo-vinyl bifunctional building block. This conversion was characterized by ‘green’ properties such as a step- and atom-economy, catalyst-free conditions, highly anti-selectivity, and readily available starting materials.

Key words

benzo[e][1,2]oxaphosphinine - β-amino-β′-hydroxyalkylphosphonate - phosphadihydrocoumarin - tetrahydroisoquinoline - intermolecular annulation

Full Text

References

References

1a Westheimer F. Science 1987; 235: 1173
1b Chan T.-H, Xin Y.-C, von Itzstein M. J. Org. Chem. 1997; 62: 3500
1c Clarion L, Jacquard C, Sainte-Catherine O, Loiseau S, Filippini D, Hirlemann M.-H, Volle J.-N, Virieux D, Lecouvey M, Pirat J.-L, Bakalara N. J. Med. Chem. 2012; 55: 2196
1d Lentini NA, Foust BJ, Hsiao C.-HC, Wiemer AJ, Wiemer DF. J. Med. Chem. 2018; 61: 8658
1e Mével M, Montier T, Lamarche F, Delépine P, Le Gall T, Yaouanc J.-J, Jaffrès P.-A, Cartier D, Lehn P, Clément J.-C. Bioconjugate Chem. 2007; 18: 1604
1f Zhuang Q, Franjesevic AJ, Corrigan TS, Coldren WH, Dicken R, Sillart S, DeYong A, Yoshino N, Smith J, Fabry S, Fitzpatrick K, Blanton TG, Joseph J, Yoder RJ, McElroy CA, Ekici ÖD, Callam CS, Hadad CM. J. Med. Chem. 2018; 61: 7034
1g Kollár L, Keglevich G. Chem. Rev. 2010; 110: 4257

2a Ravichandiran P, Lai B, Gu Y. Chem. Rec. 2017; 17: 142
2b Nefzi A, Ostresh JM, Houghten RA. Chem. Rev. 1997; 97: 449
2c Stanovnik B, Svete J. Chem. Rev. 2004; 104: 2433

3a Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
3b Lee H.-J, Cho C.-W. J. Org. Chem. 2013; 78: 3306
3c Qian H, Zhao W, Sung HH, Williams ID, Sun J. Chem. Commun. 2013; 49: 4361

4a Bedalov A, Gatbonton T, Irvine WP, Gottschling DE, Simon JA. Proc. Natl. Acad. Sci. U. S. A. 2001; 98: 15113
4b Dayde B, Pierra C, Gosselin G, Surleraux D, Ilagouma AT, Laborde C, Volle J.-N, Virieux D, Pirat J.-L. Eur. J. Org. Chem. 2014; 2014: 1333
4c Stoianova DS, Hanson PR. Org. Lett. 2001; 3: 3285
4d Barros MT, Phillips AM. F. Eur. J. Org. Chem. 2011; 2011: 402890
4e Xu J. Sci. Sin.: Chim. 2013; 43: 995

5a Kim C.-E, Ryu T, Kim S, Lee K, Lee C.-H, Lee PH. Adv. Synth. Catal. 2013; 355: 2873
5b Kim C.-E, Son J.-Y, Shin S, Seo B, Lee PH. Org. Lett. 2015; 17: 908
5c Li X, Wang Y, Fu H, Jiang Y, Zhao Y. Bioorg. Chem. 2006; 34: 105
5d Li X, Zhang D, Pang H, Shen F, Fu H, Jiang Y, Zhao Y. Org. Lett. 2005; 7: 4919
5e Li XS, Shen F, Fu H, Jiang YY, Zhao YF. Synlett 2006; 630
5f Nemtarev AV, Mironov VF, Varaksina EN, Gubaidullin AT, Krivolapov DB, Musin RZ, Litvinov IA. Russ. Chem. Bull. 2014; 63: 149
5g Petkova NI, Nikolova RD, Bojilova AG, Rodios NA, Kopf J. Tetrahedron 2009; 65: 1639

6a Jiang J, Wu M, Zhu Z, Kong D. Synthesis 2017; 49: 3731
6b Wu M, Jiang J, Zhu Z, Wang Q, Kong D. Synthesis 2018; 50: 139

7 Son JY, Kim H, Jeon WH, Baek Y, Seo B, Um K, Lee K, Lee PH. Adv. Synth. Catal. 2017; 359: 3194
8 Mantelingu K, Lin Y, Seidel D. Org. Lett. 2014; 16: 5910

9a Lee H.-S, Kang SH. Synlett 2004; 2004: 1673
9b Daniel PE, Weber AE, Malcolmson SJ. Org. Lett. 2017; 19: 3490
9c Grosser G, Baringhaus KH, Doring B, Kramer W, Petzinger E, Geyer J. Mol. Cell. Endocrinol. 2016; 428: 133
9d Kayal S, Mukherjee S. Org. Lett. 2015; 17: 5508
9e Cao Y.-M, Shen F.-F, Zhang F.-T, Zhang J.-L, Wang R. Angew. Chem. Int. Ed. 2014; 53: 1862
9f Das B, Reddy CR, Nagendra S, Lingaiah M. Tetrahedron Lett. 2011; 52: 3496
9g Mikołajczyk M, Drabowicz J, Łyżwa P. Asymmetric Synthesis of Phosphonic Analogs of (-Amino Acids . In Enantioselective Synthesis of β-Amino Acids, 2nd ed. Juaristi E, Soloshonok VA. Blackwell Science; Oxford: 2005
9h Palacios F, Alonso C, de los Santos JM. Curr. Org. Chem. 2004; 8: 1481
9i Gubnitskaya E, Peresypkina L, Samarai L. Russ. Chem. Rev. 1990; 59: 807
9j Orsini F, Sello G, Sisti M. Curr. Med. Chem. 2010; 17: 264
9k Palacios F, Alonso C, de los Santos JM. Chem. Rev. 2005; 105: 899

10a Chen W, Seidel D. Org. Lett. 2016; 18: 1024
10b Pavan Kumar CS, Harsha KB, Sandhya NC, Ramesha AB, Mantelingu K, Rangappa KS. New J. Chem. 2015; 39: 8397
10c Richers MT, Breugst M, Platonova AY, Ullrich A, Dieckmann A, Houk KN, Seidel D. J. Am. Chem. Soc. 2014; 136: 6123

11a Maury C, Gharbaoui T, Royer J, Husson H.-P. J. Org. Chem. 1996; 61: 3687
11b Schlemminger I, Saida Y, Gröger H, Maison W, Durot N, Sasai H, Shibasaki M, Martens J. J. Org. Chem. 2000; 65: 4818
11c Furegati S, Binder M, Linden A, Rüedi P. Helv. Chim. Acta 2006; 89: 1351

Supplementary Material