Transition-Metal-Based Synthesis of Dendralenes

Sangho Park; Daesung Lee

doi:10.1055/s-2007-966069

PAPER

Transition-Metal-Based Synthesis of Dendralenes

Sangho Park, Daesung Lee*
Department of Chemistry, University of Wisconsin, Madison, WI 53706, USA
Fax: +1(608)2654534; e-Mail: dlee@chem.wisc.edu;

Abstract

Alle Artikel dieser Rubrik

Abstract

The consecutive ring-closing enyne metathesis of allylsilyl propargyl ethers with Grubbs’ ruthenium-alkylidene catalyst, followed by rhenium oxide mediated 1,4-elimination of the Si-O moiety from the siloxenes, provides [3]- and [4]dendralenes in good yields.

Key words

dendralenes - enynes - ring-closing metathesis - 1,4-eliminations - rhenium oxide

Volltext

Referenzen

References

1a Hopf H. In Organic Synthesis Highlights V Schmalz H.-G. Wirth T. Wiley-VCH; Weinheim Germany: 2003. p.419-427

1b Hopf H. Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives Wiley-VCH; Weinheim Germany: 2000.

1c Hopf H. Angew. Chem. Int. Ed. 2001, 40: 705

For a conformational study, see:

1d Brian PT. Smart BA. Robertson HE. Davis MJ. Rankin DWH. Henry WJ. Gosney I. J. Org. Chem. 1997, 62: 2767

2a Blomquist AT. Verdol JA. J. Am. Chem. Soc. 1955, 77: 81

2b Blomquist AT. Verdol JA. J. Am. Chem. Soc. 1955, 77: 1806

2c Brummond KM. Chen H. Sill P. You L. J. Am. Chem. Soc. 2002, 124: 15186

2d Bräse S. Wertal H. Frank D. Vidović D. de Meijere A. Eur. J. Chem. 2005, 4167

2e Kang B. Kim D.-H. Do Y. Chang S. Org. Lett. 2003, 5: 3041

3a Tsuge O. Wada E. Kanemasa S. Chem. Lett. 1983, 1525

3b Spino C. Liu G. Tu N. Girard S. J. Org. Chem. 1994, 59: 5596

3c Tsuge O. Hatta T. Yakata K. Maeda H. Chem. Lett. 1994, 1833

3d Bräse S. de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34: 2545

3e Woo N. Legoupy S. Parra S. Fallis AG. Org. Lett. 1999, 1: 1013

3f Brummond KM. You L. Tetrahedron 2005, 61: 6180

3g Dion A. Dubé P. Spino C. Org. Lett. 2005, 7: 5601

3h Payne AD. Willis AC. Sherburn MS. J. Am. Chem. Soc. 2005, 127: 12188

3i Souweha MS. Arab A. ApSimon M. Fallis AG. Org. Lett. 2007, 9: 615

4a Fielder S. Rowan DD. Sherburn MS. Angew. Chem. Int. Ed. 2000, 39: 4331

4b Woo S. Squires N. Fallis AG. Org. Lett. 1999, 1: 573

5 Miller NA. Willis AC. Paddon-Row MN. Sherburn MS. Angew. Chem. Int. Ed. 2007, 46: 937

6 Kwon O. Park SB. Schreiber SL. J. Am. Chem. Soc. 2002, 124: 13402

7 Scholl M. Ding S. Lee CW. Grubbs RH. Org. Lett. 1999, 1: 953

8 Stragies R. Blechert S. Tetrahedron 1999, 55: 8179

9a Ahmed M. Atkinson CE. Barrett AGM. Malagu K. Procopiou PA. Org. Lett. 2003, 5: 669

9b Li F. Miller MJ. J. Org. Chem. 2006, 71: 5221

9c Kim M. Miller RL. Lee D. J. Am. Chem. Soc. 2005, 127: 12818

10 Le Nôtre J. Martinez AA. Dixneuf PH. Bruneau C. Tetrahedron 2003, 59: 9425

For reviews, see:

11a Giessert AJ. Diver ST. Chem. Rev. 2004, 104: 1317

11b Poulsen CS. Madsen R. Synthesis 2003, 1

11c Mori M. In Handbook of Metathesis Vol. 2: Grubbs RH. Wiley-VCH; Weinheim Germany: 2003. p.176

For a review on rhenium(VII) oxide, see:

12a Romão CC. Kühn FE. Herrmann WA. Chem. Rev. 1997, 97: 3197

For allylic transposition with rhenium(VII) oxide, see:

12b Le Ny J.-P. Bellemin-Laponnaz S. C. R. Chim. 2002, 217

12c Trost BM. Toste FD. J. Am. Chem. Soc. 2000, 122: 11262

12d Morrill C. Beutner GL. Grubbs RH. J. Org. Chem. 2006, 71: 7813

12e Hansen EC. Lee D. J. Am. Chem. Soc. 2006, 128: 8142

13

The stereochemistry of 8a and 8b was assigned in analogy to that of 3g.

14 Lo HC. Han H. D’Souza LJ. Sinha SC. Keinan E. J. Am. Chem. Soc. 2007, 128: 1246

15 Yao Q. Org. Lett. 2001, 3: 2069