A masked-alkene metathesis-based synthesis of isopulo'upone

Tetrahedron Letters

Volumn 52, Issue 34, 2011, Pages 4494-4496

  Carter, Kyle P ^a   Moser, Daniel J ^a   Storvick, Jennifer M ^a   O'Neil, Gregory W ^a  

^a WESTERN WASHINGTON UNIVERSITY   (United States)

Author keywords

Acyloxysulfone; Chemoselectivity; Intramolecular Diels Alder; Natural products; Olefin metathesis

Indexed keywords

ALDEHYDE; ALKENE; ISOPULO'UPONE; LITHIUM; NATURAL PRODUCT; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; DIELS ALDER REACTION; MASKED ALKENE METATHESIS BASED SYNTHESIS; OLEFINATION; SYNTHESIS;

ALNUS;

EID: 79960833878     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.082     Document Type: Article

References (25)

1. K.J. Ivin, and J.C. Mol Olefin Metathesis and Metathesis Polymerization 1997 Academic Press San Diego
2. A. Fürstner Alkene Metathesis in Organic Synthesis 1998 Springer Berlin
3. For select applications in natural product synthesis see: M.J. Mitton-Fry, A.J. Cullen, and T. Sammakia Angew. Chem., Int. Ed. 46 2007 1066 1070
4. A. Fürstner, C. Nevado, M. Waser, M. Tremblay, C. Chevrier, F. Teply, C. Aissa, E. Moulin, and O. Mueller J. Am. Chem. Soc. 129 2007 9150 9161
5. S. Bouzbouz, R. Simmons, and J. Cossy Org. Lett. 6 2004 3465 3467
6. T.W. Funk, J. Efskind, and R.H. Grubbs Org. Lett. 7 2005 187 190
7. L. Ferrié, D. Amans, S. Reymond, V. Bellosta, P. Capdeville, and J. Cossy J. Organomet. Chem. 691 2006 5456 5465
8. For examples of masked alkene metathesis in synthesis see: S. Barluenga, P.-Y. Dakas, Y. Ferandin, L. Meijer, and N. Winssinger Angew. Chem., Int. Ed. 45 2006 3951 3954
9. L.J. Baird, M.S.M. Timmer, P.H. Teesdale-Spittle, and J.E. Harvey J. Org. Chem. 74 2009 2271 2277
10. R. Dumeunier, and I.E. Markó The Julia Reaction T. Takeshi, Modern Carbonyl Olefination 2004 Wiley-VCH Weinheim
11. G.W. O'Neil, D.J. Moser, and E.O. Volz Tetrahedron Lett. 50 2009 7355 7357
12. For a recent review see: S.P. Nolan, and H. Clavier Chem. Soc. Rev. 39 2010 3305 3316
13. A.K. Chatterjee, T.-L. Choi, D.P. Sanders, and R.H. Grubbs J. Am. Chem. Soc. 125 2003 11360 11370
14. H. Yang, and R.G. Carter Org. Lett. 12 2010 3108 3111
15. T.M. Trnka, and R.H. Grubbs Acc. Chem. Res. 34 2001 18 29
16. G.E. Keck, K.A. Savin, and M.A. Weglarz J. Org. Chem. 60 1995 3194 3204
17. I.E. Marko, F. Murphy, L. Kumps, A. Ates, R. Touillaux, D. Craig, S. Carballares, and S. Dolan Tetrahedron 57 2001 2609 2619
18. T.R. Hoye, and H. Zhao Org. Lett. 1 1999 1123 1125
19. For additional examples see Ref. 7.
20. For a recent review see: M. Juhl, and D. Tanner Chem. Soc. Rev. 38 2009 2983 2992
21. A. Spinella, L.A. Alvarez, and G. Cimino Tetrahedron 49 1993 3203 3210
22. J. Matikainan, S. Kaltia, and T. Hase Synth. Commun. 25 1995 195 201
23. D.A. Evans, and J.S. Johnson J. Org. Chem. 62 1997 786 787
24. S. Nanda Tetrahedron Lett. 46 2005 3661 3663
25. See Supplementary data for details.