Synthesis, Inhaltsverzeichnis Synthesis 2019; 51(10): 2207-2213DOI: 10.1055/s-0037-1612248 paper © Georg Thieme Verlag Stuttgart · New YorkA Free-Radical and Protecting-Group-Free Approach to (–)-Boschnialactone and γ-Lycorane Alberto Basante-Avendaño , Víctor E. Guerra-Ayala , Alma Sánchez-Eleuterio , Alejandro Cordero-Vargas * Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, Coyoacán, 04510 Mexico City, Mexico eMail: acordero@unam.mx› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik ◊ Contributed equally to this work Abstract The protecting-group-free (PGF) and free-radical-based synthesis of two structurally different natural products, (–)-boschnialactone and γ-lycorane, is reported. The key step in both syntheses is a radical–ionic sequence for construction of the principal structure (a six-membered lactone and a 1,4-dicarbonyl compound, respectively), allowing short and rapid access to these natural products through a PGF route. Key words Key wordsradicals - protecting-group-free synthesis - atom-transfer radical addition - ATRA - boschnialactone - lycorane Volltext Referenzen References 1 Kocieński PJ. Protecting Groups, 2nd ed. Thieme; Stuttgart: 2000 2 Protecting-Group-Free Organic Synthesis. Fernandes RA. Wiley; Hoboken, NJ: 2018 3 Peralta-Hernández E, Cortezano-Arellano O, Cordero-Vargas A. Tetrahedron Lett. 2011; 52: 6899 4 Morales-Chamorro M, Meza-González J, Cordero-Vargas A. Tetrahedron Lett. 2015; 56: 4892 5 Peralta-Hernández E, Blé-González EA, Gracia-Medrano-Bravo VA, Cordero-Vargas A. Tetrahedron 2015; 71: 2234 6 León-Rayo DF, Morales-Chamorro M, Cordero-Vargas A. Eur. J. Org. Chem. 2016; 1739 7 Sakan T, Murai F, Hayashi Y, Honda Y, Shono T, Nakajima M, Kato M. Tetrahedron 1967; 23: 4635 8a Callant P, Storme P, Van der Eycken E, Vanderwalle M. Tetrahedron Lett. 1983; 24: 5797 8b Storme P, Quaeghebeur L, Vandewalle M. Bull. Soc. Chim. Belg. 1984; 93: 999 8c Caille CJ, Tabyaoui B, Guilard R. Synth. Commun. 1985; 15: 669 8d Wang T.-F, Yang C.-F. J. Chem. Soc., Chem. Commun. 1989; 1876 8e Hanquet B, Tabyaoui B, Caille J.-C, Farner M, Guilard R. Can. J. Chem. 1990; 68: 620 8f Chiu J.-Y, Chiu C.-T, Chang N.-C. J. Chin. Chem. Soc. 1997; 44: 59 8g Chang M.-Y, Lin C.-H, Lee A.-Y, Tai H.-M, Chang N.-C. J. Chin. Chem. Soc. 1999; 46: 205 8h Taniguchi T, Goto Y, Ogasawa K. Synlett 1997; 707 9a Arai Y, Kawanami S, Koizumi T. Chem. Lett. 1990; 1585 9b Arai Y, Kawanami S, Koizumi T. J. Chem. Soc., Perkin Trans. 1 1991; 2969 9c Tanaka D, Yoshino T, Kuono I, Miyashita M, Irie H. Tetrahedron 1993; 49: 10253 9d Nangia A, Prasuna G, Rao B. Tetrahedron Lett. 1994; 35: 3755 9e Chavez DE, Jacobsen EN. Org. Lett. 2003; 5: 2563 9f Inoue T, Kitigawa O, Saito A, Taguchi T. J. Org. Chem. 1997; 62: 7384 10 Kotera K. Tetrahedron 1961; 12: 248 11a Umezawa B, Hochino O, Sawaki S, Sato S, Numao N. J. Org. Chem. 1977; 42: 4272 11b Bäckvall J.-E, Andersson PG, Stone GB, Gogoll A. J. Org. Chem. 1991; 56: 2988 11c Banwell MG, Wu AW. J. Chem. Soc., Perkin Trans. 1 1994; 2671 11d Cossy J, Tresnard L, Gómez-Pardo D. Tetrahedron Lett. 1999; 40: 1125 11e Cassayre J, Zard SZ. Synthesis 1999; 501 11f Padwa A, Brodney MA, Lynch SM. J. Org. Chem. 2001; 66: 1716 11g Gao S, Tu YQ, Song Z, Wang A, Fan X, Jiang Y. J. Org. Chem. 2005; 70: 6523 11h Huntley RJ, Funk RL. Tetrahedron Lett. 2011; 52: 6671 11i Conner ES, Crocker KE, Fernando RG, Froncsek FR, Stanley GG, Ragains JR. Org. Lett. 2013; 15: 5558 11j Liu D, Ai L, Zhao A, Chen J, Zhang H, Liu J. Org. Biomol. Chem. 2014; 12: 3191 11k Doan BN. D, Tan XY, Ang CM, Bates RW. Synthesis 2017; 49: 4711 11l Monaco A, Szulc BR, Rao ZX, Barniol-Xicota M, Sehailia M, Borges BM. A, Hilton ST. Chem. Eur. J. 2017; 23: 4750 11m Ho GM, Li Y.-J. Asian J. Org. Chem. 2018; 7: 145 11n Osornio YM, Miranda LD. Rev. Soc. Quim. Mex. 2004; 48: 288 12a Yoshizaki H, Satoh H, Sato Y, Nukui S, Shibasaki M, Mori M. J. Org. Chem. 1995; 60: 2016 12b Ikeda M, Ohtani S, Sato T, Ishibashi H. Synthesis 1998; 1803 12c Dong L, Xu Y.-J, Cun L.-F, Cui X, Mi A.-Q, Jiang Y.-Z, Gong L.-Z. Org. Lett. 2005; 7: 4285 12d Dong L, Xu Y.-J, Yuan W.-C, Cui X, Cun L.-F, Gong L.-Z. Eur. J. Org. Chem. 2006; 4093 12e Chapsal BD, Ojima I. Org. Lett. 2006; 8: 1395 12f El Bialy SA. A. Nat. Prod. Res. 2008; 22: 1176 12g Liu C, Xie J.-H, Li Y.-L, Chen J.-Q, Zhou Q.-L. Angew. Chem. Int. Ed. 2013; 52: 593 13 Field LD, Gallagher SP. Tetrahedron Lett. 1985; 26: 6125 14 Erikkilä A, Pihko PM. J. Org. Chem. 2006; 71: 2538 Zusatzmaterial Zusatzmaterial Supporting Information
