38.8. 3.2 Stable and Unstable 1,2-Dioxolanes: Origin, Synthesis, and Biological Activities
Book
Editors: Christmann, M.; Huang, Z.; Joule, J. A.; Li, C.-J.; Li, J. J.; Marschner, C.; Petersson, E. J.; Reissig, H.-U.; Terent'ev, A. O.
Title: Knowledge Updates 2020/2
Print ISBN: 9783132435612; Online ISBN: 9783132435636; Book DOI: 10.1055/b000000103
1st edition © 2020 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract

This chapter describes 1,2-dioxolanes, with confirmed biological activity, isolated from various natural sources. The key steps in the formation of the 1,2-dioxolane ring in the total synthesis of some natural peroxides as well as interesting modern procedures for the synthesis of 1,2-dioxolanes are also presented.
Key words
1,2-dioxolanes - peroxides - oxidation - oxygen - hydrogen peroxide - hydroperoxides - cyclopropanes - acetylenes - carbonyl compounds - ketones - alkenes - enones - ketals - acetals - epoxides - allenes - nitrosoarenes - ozonolysis - antimalarial - antifungal - antiviral - anticancer- 5 Vil VA, Gloriozova TA, Poroikov VV, Terent’ev AO, Savidov N, Dembitsky VM. Appl. Microbiol. Biotechnol. 2018; 102: 7657
- 10 The authors wish to express their gratitude to the Russian Foundation for Basic Research (Grant No. 18–53–15010) for financial support.
- 13 Marco JA, Sanz-Cervera JF, Ropero FJ, Batlle N, Guara M, Vallès-Xirau J. Phytochemistry 1998; 47: 1417
- 22 Manriquez V, Labbé C, Castillo M, von Schnering HG, Peters K. Acta Crystallogr., Sect. C 1990; 46: 802
- 28 Li P, Matsunaga K, Yamamoto K, Yoshikawa R, Kawashima K, Ohizumi Y. Neurosci. Lett. 1999; 273: 53
- 31 Zaugg J, Eickmeier E, Ebrahimi SN, Baburin I, Hering S, Hamburger M. J. Nat. Prod. 2011; 74: 1437
- 34 Saito Y, Hattori M, Iwamoto Y, Takashima Y, Mihara K, Sasaki Y, Fujiwara M, Sakaoku M, Shimizu A, Chao X, Kuroda C, Gong X, Hanai R, Tori M. Tetrahedron 2011; 67: 2220
- 35 Ma J.-H, Wang Y, Liu Y, Gao S.-Y, Ding L.-Q, Zhao F, Chen L.-X, Qiu F. J. Asian Nat. Prod. Res. 2015; 17: 532
- 36 Crombie L, Games DE, Haskins NJ, Reed GF, Finnegan RA, Merkel KE. Tetrahedron Lett. 1970; 11: 3975
- 42 Kastner U, Breuer J, Glasl S, Baumann A, Robien W, Jurenitsch J, Rücker G, Kubelka W. Planta Med. 1995; 61: 83
- 44 Hewlett MJ, Begley MJ, Groenewegen WA, Heptinstall S, Knight DW, May J, Salan U, Toplis D. J. Chem. Soc., Perkin Trans. 1 1996; 1979
- 47 Scott JJ, Oh D.-C, Yuceer MC, Klepzig KD, Clardy J, Currie CR. Science (Washington, D. C.) 2008; 322: 63
- 49 Yaoita Y, Matsuki K, Iijima T, Nakano S, Kakuda R, Machida K, Kikuchi M. Chem. Pharm. Bull. 2001; 49: 589
- 51 Vieira IJC, Figueiredo ER, Vieira MGC, de Carvalho Jr AR, Passos MDS, Boeno SIDS, Azevedo OA, Braz-Filho R. Molecules 2018; 23: 949
- 54 He F, Pu J.-X, Huang S.-X, Wang Y.-Y, Xiao W.-L, Li L.-M, Liu J.-P, Zhang H.-B, Li Y, Sun H.-D. Org. Lett. 2010; 12: 1208
- 55 Chen G.-F, Li Z.-L, Chen K, Tang C.-M, He X, Pan D.-J, Mcphail DR, Mcphail AT, Lee K.-H. Tetrahedron Lett. 1990; 31: 3413
- 56 He W.-J, Chu H.-B, Zhang Y.-M, Han H.-J, Yan H, Zeng G.-Z, Fu Z.-H, Olubanke O, Tan N.-H. Planta Med. 2011; 77: 1924
- 58 Guo H, Yao S, Yang X, Chen Y, Chen Y, Gong F, Tong J, Qian J, Zhang A, Cai X. Nat. Prod. Res. 2018; 32: 1817
- 60 Mohammed R, Peng J, Kelly M, Yousaf M, Winn E, Odde S, Bie Z, Xie A, Doerksen RJ, Hamann MT. Aust. J. Chem. 2010; 63: 877
- 61 Santos EA, Quintela AL, Ferreira EG, Sousa TS, Pinto FDCL, Hajdu E, Carvalho MS, Salani S, Rocha DD, Wilke DV, Torres MDCM, Jimenez PC, Silveira ER, La Clair JJ, Pessoa ODL, Costa-Lotufo LV. J. Nat. Prod. 2015; 78: 996
- 63 Schirmeister T, Oli S, Wu H, Della Sala G, Costantino V, Seo E.-J, Efferth T. Mar. Drugs 2017; 15: 63
- 64 Rudi A, Afanii R, Gravalos LG, Aknin M, Gaydou E, Vacelet J, Kashman Y. J. Nat. Prod. 2003; 66: 682
- 67 Chen Y, Killday KB, McCarthy PJ, Schimoler R, Chilson K, Selitrennikoff C, Pomponi SA, Wright AE. J. Nat. Prod. 2001; 64: 262
- 68 Jiménez-Romero C, Ortiz I, Vicente J, Vera B, Rodríguez AD, Nam S, Jove R. J. Nat. Prod. 2010; 73: 1694
- 71 Frimer AA, Afri M, Baumel SD, Gilinsky-Sharon P, Rosenthal Z, Gottlieb HE. J. Org. Chem. 2000; 65: 1807
- 73 Gao J.-F, Xie J.-H, Harimaya K, Kawamata T, Iitaka Y, Inayama S. Chem. Pharm. Bull. 1991; 39: 854
- 78 Kirihara M, Kakuda H, Ichinose M, Ochiai Y, Takizawa S, Mokuya A, Okubo K, Hatano A, Shiro M. Tetrahedron 2005; 61: 4831
- 92 Gaschler MM, Andia AA, Liu H, Csuka JM, Hurlocker B, Vaiana CA, Heindel DW, Zuckerman DS, Bos PH, Reznik E, Ye LF, Tyurina YY, Lin AJ, Shchepinov MS, Chan AY, Peguero-Pereira E, Fomich MA, Daniels JD, Bekish AV, Shmanai VV, Kagan VE, Mahal LK, Woerpel KA, Stockwell BR. Nat. Chem. Biol. 2018; 14: 507
- 98 Brindisi M, Gemma S, Kunjir S, Di Cerbo L, Brogi S, Parapini S, D’Alessandro S, Taramelli D, Habluetzel A, Tapanelli S, Lamponi S, Novellino E, Campiani G, Butini S. MedChemComm 2015; 6: 357
- 101 Terent’ev AO, Yaremenko IA, Chernyshev VV, Dembitsky VM, Nikishin GI. J. Org. Chem. 2012; 77: 1833
- 104 Ingram K, Yaremenko IA, Krylov IB, Hofer L, Terent’ev AO, Keiser J. J. Med. Chem. 2012; 55: 8700