Synthesis of New Polycyclic β-Lactams via One-Pot Enyne Metathesis and Diels-Alder Reactions

Abstract

One-pot ring-closing enyne metathesis and Diels-Alder reactions led to efficient synthesis of tricyclic and tetracyclic β-lactams.

Key words

metathesis - Diels-Alder cycloaddition - one-pot reactions - polycycles - lactams

References

• 1 Tietze LF. Beifuss U. Angew. Chem., Int. Ed. Engl.  1993,  32:  131 
• For recent examples of one-pot enyne metathesis and Diels-Alder reactions, see:
• 2a Kotha S. Sreenivasachary N. Brahmachary E. Tetrahedron Lett.  1998,  39:  2805 
• 2b Schürer SC. Blechert S. Tetrahedron Lett.  1999,  40:  1877 
• 2c Stragies R. Voigtmann U. Blechert S. Tetrahedron Lett.  2000,  41:  5465 
• 2d Bentz D. Laschat S. Synthesis  2000,  1766 
• 2e Rodriguez JR. Castedo L. Mascareñas JL. Chem.-Eur. J.  2002,  8:  2923 
• 2f Banti D. North M. Adv. Synth. Catal.  2002,  344:  694 
• 2g Rosillo M. Dominguez G. Casarrubios L. Amador U. Perez-Castells J. J. Org. Chem.  2004,  69:  2084 
• 3a Katz TJ. Sivavec TM. J. Am. Chem. Soc.  1985,  107:  737 
• 3b Kinoshita A. Mori M. Synlett  1994,  1020 
• 3c For a recent review on enyne metathesis, see: Poulsen CS. Madsen R. Synthesis  2003,  1 
• 4a Fringuelli F. Taticchi A. The Diels-Alder Reaction: Selected Pratical Methods   Wiley and Sons; Chichester: 2002. 
• 4b Corey EJ. Angew. Chem. Int. Ed.  2002,  41:  1650 
• 4c Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis G. Angew. Chem. Int. Ed.  2002,  41:  1668 
• 5a Dürckheimer W. Blumbach J. Lattrell R. Scheunemann KH. Angew. Chem., Int. Ed. Engl.  1985,  24:  180 
• 5b Cabri W. Di Fabio R. From Bench to Market   Oxford University Press; Oxford: 2000. 
• 5c Recent Progress in the Chemical Synthesis of Antibiotics   Lukacs G. Ohno M. Springer; Berlin: 1990. 
• 5d Mann J. The Elusive Magic Bullet: The Search for the Perfect Drug   Oxford University Press; Oxford: 1999. 
• 5e Hamilton-Miller JMT. J. Antimicrob. Chemother.  1999,  44:  729 
• 6 For a review, see: Alcaide B. Almendros P. Curr. Org. Chem.  2002,  6:  245 
• For other syntheses of bi- and tricyclic β-lactams via metathesis, see:
• 7a Barrett AGM. Baugh SPD. Braddock DC. Flack K. Gibson VC. Giles MR. Marshall EL. Procopiou PA. White AJP. Williams DJ. J. Org. Chem.  1998,  63:  7893 
• 7b Barrett AGM. Ahmed M. Baker SP. Baugh SPD. Braddock DC. Procopiou PA. White AJP. Williams DJ. J. Org. Chem.  2000,  65:  3716 
• 7c Alcaide B. Almendros P. Alonso JM. Aly MF. Redondo MC. Synlett  2001,  773 
• Recent references:
• 8a Desroy N. Le Roux R. Phansavath P. Chiummiento L. Bonini C. Genêt J.-P. Tetrahedron Lett.  2003,  44:  1763 
• 8b Labeeuw O. Phansavath P. Genêt JP. Tetrahedron Lett.  2003,  44:  6383 
• 8c Michelet V. Adiey K. Tanier S. Dujardin G. Genêt J.-P. Eur. J. Org. Chem.  2003,  2947 
• 8d Mordant C. Caño de Andrade C. Touati R. Ratovelomanana-Vidal V. Ben Hassine B. Genet JP. Synthesis  2003,  2405 
• 9a Roland S. Durand JO. Savignac M. Genêt J.-P. Tetrahedron Lett.  1995,  36:  3007 
• 9b Roland S. Savignac M. Durand JO. Genêt J.-P. Bull. Soc. Chim. Fr.  1996,  133:  945 
• 9c Galland JC. Roland S. Malpart J. Savignac M. Genêt J.-P. Eur. J. Org. Chem.  1999,  621 
• 9d For a recent discussion of syntheses of carbapenams using transition metals, see: Mori M. Kozawa Y. Takimoto M. J. Synth. Org. Chem. Jpn.  2003,  61:  1065 
• 10 Duboc R. Hénaut C. Savignac M. Genêt J.-P. Bhatnagar N. Tetrahedron Lett.  2001,  42:  2461 
• 11a For a review on the synthesis of the azetidinone, see: Berks AH. Tetrahedron  1996,  52:  331 
• 11b Noyori R. Ikeda T. Okhuma T. Widhalm M. Kitamura M. Takaya H. Akutagawa S. Sayo N. Saito T. Taketomi T. Kumobayashi H. J. Am. Chem. Soc.  1989,  111:  9134 
• 11c Murahashi SI. Naota T. Kuwabara T. Saito T. Kumobayashi H. Akutagawa S. J. Am. Chem. Soc.  1990,  112:  7820 
• 12a Trnka TM. Grubbs RH. Acc. Chem. Res.  2001,  34:  18 
• 12b Schwab P. Grubbs RH. Ziller JW. J. Am. Chem. Soc.  1996,  118:  100 
• 13 For a review on non-metathetic behavior of Grubbs’ catalyst, see: Alcaide B. Almendros P. Chem.-Eur. J.  2003,  9:  1258 
• 15 Nakai T, and Chiba T. inventors; U.S. Patent  4845210. 
• 16 Moseley K. Maitlis PM. J. Chem. Soc., Dalton Trans.  1974,  169 

14

Reaction between DMAD and 5 mol% of Grubbs’ catalyst or other ruthenium(II) sources {(cod)Ru(Met)₂, [(p-cymene)RuCl]₂} in CH₂Cl₂ at 80 °C also led to low yields (10-15%) of hexamethyl mellitate 19.