Snyder, S. A.: 2016 Science of Synthesis, 2015/4a: Applications of Domino Transformations in Organic Synthesis 1 DOI: 10.1055/sos-SD-219-00044
Applications of Domino Transformations in Organic Synthesis 1

1.2 Cation–π Cyclizations of Epoxides and Polyepoxides

Weitere Informationen

Buch

Herausgeber: Snyder, S. A.

Autoren: Adu-Ampratwum, D.; Anderson, E. A.; Armbrust, K. W.; Devery, J. J.; Douglas, J.; Doyle, M. P.; Engle, K. M.; Forsyth, C. J.; Gille, F.; Halkina, T.; Hu, X.; Jamison, T.; Kelley, E. H.; Kirschning, A.; Lee, D.; Maimone, T. J.; Merino, E.; Nevado, C.; O'Connor, M.; Ohshima, T.; Parker, K. A.; Renata, H.; Salvador, A.; Shenvi, R. A.; Shi, L.; Sittihan, S.; Stephenson, C. R. J.; Tang, M.; Truong, P.; Tu, Y.-Q.; Wan, K. K.; Wang, S.-H.; Wolling, M.; Xu, X.; Yang, Z.

Titel: Applications of Domino Transformations in Organic Synthesis 1

Print ISBN: 9783131731319; Online ISBN: 9783132402522; Buch-DOI: 10.1055/b-003-128286

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Typ: Mehrbändiges Werk

 


K. W. Armbrust; T. Halkina; E. H. Kelley; S. Sittihan; T. Jamison

Abstract

Zoom

This chapter describes the formation of complex polycyclic fragments from linear epoxide and polyepoxide precursors via domino reactions. Depending on the reaction conditions employed, either exo or endo epoxide opening can be selectively achieved. Applications of these domino reactions toward the synthesis of complex natural products are discussed.

 
  • 4 Baldwin JE. J. Chem. Soc., Chem Commun. 1976; 734
  • 9 Iimori T, Still WC, Rheingold AL, Staley DL. J. Am. Chem. Soc. 1989; 111: 3439
  • 11 Morimoto Y, Iwai T, Nishikawa Y, Kinoshita T. Tetrahedron: Asymmetry 2002; 13: 2641
  • 15 Bravo F, McDonald FE, Neiwert WA, Do B, Hardcastle KI. Org. Lett. 2003; 5: 2123
  • 17 McDonald FE, Bravo F, Wang X, Wei X, Toganoh M, Rodríguez JR, Do B, Neiwert WA, Hardcastle KI. J. Org. Chem. 2002; 67: 2515
  • 18 Underwood BS, Tanuwidjaja J, Ng S.-S, Jamison TF. Tetrahedron 2013; 69: 5205
  • 19 Valentine JC, McDonald FE, Neiwert WA, Hardcastle KI. J. Am. Chem. Soc. 2005; 127: 4586
  • 20 Simpson GL, Heffron TP, Merino E, Jamison TF. J. Am. Chem. Soc. 2006; 128: 1056
  • 21 Tanuwidjaja J, Ng S.-S, Jamison TF. J. Am. Chem. Soc. 2009; 131: 12084
  • 22 Neverov AA, Feng HX, Hamilton K, Brown RS. J. Org. Chem. 2003; 68: 3802
  • 23 Wan S, Gunaydin H, Houk KN, Floreancig PE. J. Am. Chem. Soc. 2007; 129: 7915
  • 26 Vilotijevic I, Jamison TF. Science (Washington, D. C.) 2007; 317: 1189
  • 27 Morten CJ, Byers JA, Van Dyke AR, Vilotijevic I, Jamison TF. Chem. Soc. Rev. 2009; 38: 3175
  • 33 Tong R, Valentine JC, McDonald FE, Cao R, Fang X, Hardcastle KI. J. Am. Chem. Soc. 2007; 129: 1050
  • 35 Boone MA, Tong R, McDonald FE, Lense S, Cao R, Hardcastle KI. J. Am. Chem. Soc. 2010; 132: 5300
  • 36 Zhao J.-F, Zhao Y.-J, Loh T.-P. Chem. Commun. (Cambridge) 2008; 1353