Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2015; 26(04): 467-470
DOI: 10.1055/s-0034-1378924
DOI: 10.1055/s-0034-1378924
letter
A Rapid and Stereocontrolled Synthesis of the Zizaane Ring System by Using an Intramolecular (4+3) Cycloaddition Reaction
Further Information
Publication History
Received: 12 September 2014
Accepted after revision: 12 October 2014
Publication Date:
06 November 2014 (online)
Abstract
We report herein a very short synthetic approach to the tricyclo[6.2.1.01,5]undecane scaffold through a convergent and stereocontrolled route by using an intramolecular (4+3) cycloaddition of a simple furfuryl alcohol precursor with a pendant cyclopentadiene moiety. The formation of alternative reaction products under various conditions is also discussed.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378915. Included are experimental details and analytical results for compounds 1–6.
- Supporting Information
-
References
- 1 Wetzel S, Bon RS, Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2011; 50: 10800
- 2a Gurthler H, Pedersen R, Anthoni U, Christophersen C, Nielsen PH, Wellington EM. H, Pedersen C, Bock K. J. Antibiot. (Tokyo) 1994; 47: 434
- 2b Komae H, Nigam IC. J. Org. Chem. 1968; 33: 1771
- 2c Dwivedi GR, Gupta S, Roy S, Kalani K, Pal A, Thakur JP, Saikia D, Sharma A, Darmwal NS, Darokar MP, Srivastava SK. Chem. Biol. Drug Des. 2013; 82: 587
- 3a Barrero AF, Alvarez-Manzaneda E, Lara A. Tetrahedron Lett. 1996; 37: 3757
- 3b Yang XW, Peng K, Liu Z, Zhang GY, Li J, Wang N, Steinmetz A, Liu Y. J. Nat. Prod. 2013; 76: 2360
- 4 Mander LN. Chem. Rev. 1992; 92: 573
- 5a Coates RM, Sowerby RL. J. Am. Chem. Soc. 1972; 94: 5386
- 5b Stork G, Boeckman RK, Taber DF, Still WC, Singh J. J. Am. Chem. Soc. 1979; 101: 7107
- 5c Barker AJ, Pattenden G. Tetrahedron Lett. 1980; 21: 3513
- 5d Grootaert WM, De Clercq PJ. Tetrahedron Lett. 1986; 27: 1731
- 5e Markó IE, Seres P, Evans GR, Swarbick TM. Tetrahedron Lett. 1993; 34: 7305
- 5f Kim S, Cheong JH. Synlett 1997; 947
- 5g Chandra Pati L, Roy A, Mukherjee D. Tetrahedron Lett. 2000; 41: 10353
- 5h Banwell MG, Phillis AT, Willis AC. Org. Lett. 2006; 8: 5341
- 5i Moritz BJ, Mack DJ, Tong L, Thomson RJ. Angew. Chem. Int. Ed. 2014; 53: 2988
- 6a Hoffmann HM. R, Henning R. Helv. Chim. Acta 1983; 66: 828
- 6b Hoffmann HM. R, Henning R, Lalko OR. Angew. Chem. Int. Ed. 1982; 21: 442
- 6c Hoffmann HM. R, Eggert U, Gibbels U, Giesel K, Koch O, Lies R, Rabe J. Tetrahedron 1988; 44: 3899
- 7a Pattenden G, Winne JM. Tetrahedron Lett. 2009; 50: 7310
- 7b Winne JM, Catak S, Waroquier M, Van Speybroeck V. Angew. Chem. Int. Ed. 2011; 50: 11990
- 8 Laplace DR, Verbraeken B, Van Hecke K, Winne JM. Chem. Eur. J. 2014; 20: 253
- 9 This observation is also of interest in light of our initial mechanistic rationalization for this type of reactions (see reference 7a), and also in light of some biogenetic speculations on the role of furanoxonium-mediated processes in cembranoid-derived natural products. See also: Li Y, Palframan MJ, Pattenden G, Winne JM. Tetrahedron 2014; 70: 7229
- 10 Hullaert J, Laplace DR, Winne JM. Eur. J. Org. Chem. 2014; 3097
- 11 For further indications of a stepwise pathway in these reactions, see references 7b, 8, 10, and: Palframan MJ, Pattenden G. Synlett 2013; 24: 2720
For a selection of classical and more recent synthetic approaches, see: