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DOI: 10.1055/s-0029-1219278
Cobalt-Catalyzed Generation of 1,4-Dienes as Synthons for 1,3-Dicarbonyl Compounds and Their Application in Natural Product Syntheses
Publication History
Publication Date:
25 January 2010 (online)
Abstract
The cobalt-catalyzed 1,4-hydrovinylation of alkenes with 1,3-dienes and the cobalt-catalyzed Diels-Alder reaction of alkynes with 1,3-dienes lead to acyclic and cyclic 1,4-dienes, respectively. These products can be transformed into 1,3-dicarbonyl functional groups by ozonolysis or alternative carbon-carbon double bond cleaving reactions. The application towards the synthesis of hepialone and a pyranone-type lipid from Vanilla beans is described.
Key words
cobalt - cycloaddition - 1,3-dicarbonyl compounds - Diels-Alder - hydrovinylation - ozonolysis
- 1a Leading
reference: Chem. Rev.
1997,
97:
2463-2706 ; this special issue gives
a comprehensive introduction into biochemical and biological aspects
of polyketides
- 1b See also:
Sattely ES.Fischbach MA.Walsh CT. Nat. Prod. Rep. 2008, 25: 757 - 2 For a comprehensive review, see:
Hilt G.Weske DF. Chem. Soc. Rev. 2009, 38: 3082 - 3
Birch AJ. J. Chem. Soc. 1944, 430 - 4
Tung JC.Chen MW.Noll BC.Taylor RE.Fields SC.Dent WH.Green FR. Synthesis 2007, 2388 - 5a
Hilt G.Janikowski J.Hess W. Angew. Chem. Int. Ed. 2006, 45: 5206 - 5b
Hilt G.Janikowski J. Org. Lett. 2009, 11: 774 - 6a
Hilt G.du Mesnil F.-X.Lüers S. Angew. Chem. Int. Ed. 2001, 40: 387 - 6b
Hilt G.Lüers S. Synthesis 2002, 609 - 6c
Hilt G.Lüers S.Schmidt F. Synthesis 2003, 634 - 8a For 7a, see:
Axenrod T.Mangiaracina P.Watnick CM.Wieder MJ.Bulusu S. Org. Magn. Reson. 1980, 13: 197 - 8b For 7b,
see:
Alberola A.Andres C.Gonzalez Ortega A.Pedrosa R. J. Heterocycl. Chem. 1984, 21: 1575 - 9a
Rao BV.Rao AS. Synth. Commun. 1995, 25: 1531 - 9b
Kubo I.Matsumoto T.Wagner DL. Tetrahedron Lett. 1985, 26: 563 - 10a
MacDonald FK.Burnell DJ. J. Org. Chem. 2009, 74: 6973 - 10b
Wang H.Shuhler BJ.Xian M. J. Org. Chem. 2007, 72: 4280 - 10c
Zhang J.Li Y.Wang W.She X.Pan X. J. Org. Chem. 2006, 71: 2918 - 10d
Calad SA.Ćiraković J.Woerpel KA. J. Org. Chem. 2006, 72: 1027 - 10e
Jin M.Taylor RE. Org. Lett. 2005, 7: 1303 - 11
Ramaroson-Raonizafinimanana B.Gaydou EM.Bombarda I. J. Agric. Food Chem. 1999, 47: 3202 - 12 For the generation of oxygen-free
ozone, see experimental section and:
Schutt WS.Sigman ME.Li Y. Anal. Chim. Acta 1996, 319: 369
References
Ligands such as 2,4,6-trimethyl-N-(pyridin-2-ylmethyl-ene)aniline (as a representative of a pyridine-imine-type ligand) as well as N,N"-dibutylethane-1,2-diimine or N,N"-dicyclohexylethane-1,2-diimine (diimine-type ligands) can be applied.