Synthesis of Tetracyclic Molecules Containing Medium-Sized Heterocycles: Scope Expansion of Cascade Nicholas and Pauson–Khand Methodology

Abstract

Unique tetracyclic molecules containing heteroatom-embedded, medium-sized rings were synthesized by employing cascade Nicholas and Pauson–Khand cyclization reactions. We successfully established a divergent synthetic route for quick access to unprecedented multi-ring systems via an alkyne cobalt complex, and an expanded substrate scope for this methodology was realized.

Key words

tetracycles - medium-ring compounds - cascade cyclization - Nicholas reaction - Pauson–Khand reaction - cobalt-alkyne complex

• References

• 1a Hussain A, Yousuf SK, Mukherjee D. RSC Adv. 2014; 4: 43241
• 1b Sharma A, Appukkuttan P, Van der Eycken E. Chem. Commun. 2012; 48: 1623
• 1c Majhi TP, Achari B, Chattopadhyay P. Heterocycles 2007; 71: 1011
• 2a Molander GA. Acc. Chem. Res. 1998; 31: 603
• 2b Illuminati G, Mandolini L. Acc. Chem. Res. 1981; 14: 95
• 3a van den Broek SA. M. W, Meeuwissen SA, van Delft FL, Rutjes FP. J. T. Natural Products Containing Medium-Sized Nitrogen Heterocycles Synthesized by Ring-Closing Alkene Metathesis. In Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts. Cossy J, Arseniyadis S, Meyer C. Wiley-VCH; Weinheim: 2010: 45
• 3b Chattopadhyay SK, Karmakar S, Biswas T, Majumdar KC, Rahaman H, Roy B. Tetrahedron 2007; 63: 3919
• 3c Mori M, Kitamura T, Sato Y. Synthesis 2001; 654
• 3d Maier ME. Angew. Chem. Int. Ed. 2000; 39: 2073
• 3e Yet L. Chem. Rev. 2000; 100: 2963
• 4a Kaneda K, Fujita M, Naruse R. Heterocycles 2016; 92: 291
• 4b Asamizu T, Naruse R, Yongxue G, Kaneda K. Tetrahedron Lett. 2015; 56: 4674
• 5a Closser KD, Quintal MM, Shea KM. J. Org. Chem. 2009; 74: 3680
• 5b Shea KM, Closser KD, Quintal MM. J. Org. Chem. 2005; 70: 9088
• 5c Quintal MM, Closser KD, Shea KM. Org. Lett. 2004; 6: 4949
• 6a Röse P, Hilt G. Synthesis 2016; 48: 463
• 6b Omae I. Appl. Organomet. Chem. 2007; 21: 318
• 7a Kann N. Curr. Org. Chem. 2012; 16: 322
• 7b Teobald BJ. Tetrahedron 2002; 58: 4133
• 7c Green JR. Curr. Org. Chem. 2001; 5: 809
• 7d Müller TJ. J. Eur. J. Org. Chem. 2001; 2021
• 7e Nicholas KM. Acc. Chem. Res. 1987; 20: 207
• 8a The Pauson–Khand Reaction: Scope, Variations and Applications. Torres RR. John Wiley & Sons Ltd; New York: 2012
• 8b Lee H.-W, Kwong F.-Y. Eur. J. Org. Chem. 2010; 789
• 8c Moulton BE. The Pauson–Khand Reaction . In Organometallic Chemistry . Vol. 36. Fairlamb I, Lynam J. RCS; London: 2010: 93
• 8d Blanco-Urgoiti J, Añorbe L, Pérez-Serrano L, Domínguez G, Pérez-Castells J. Chem. Soc. Rev. 2004; 33: 32
• 8e Schore NE. Org. React. 1991; 40: 1
• 8f Khand IU, Knox GR, Pauson PL, Watts WE, Foreman MI. J. Chem. Soc., Perkin Trans. 1 1973; 977
• 9a Pérez-Castells J. Top. Organomet. Chem. 2006; 19: 207
• 9b Fletcher AJ, Christie SD. R. J. Chem. Soc., Perkin Trans. 1 2000; 1657
• 9c Jamison TF, Shambayati S, Crowe WE, Schreiber SL. J. Am. Chem. Soc. 1997; 119: 4353
• 9d Jeong N, Yoo S, Lee SJ, Lee SH, Chung YK. Tetrahedron Lett. 1991; 32: 2137
• 9e Schreiber SL, Sammakia T, Crowe WE. J. Am. Chem. Soc. 1986; 108: 3128
• 10a Swamy KK, Kumar NB, Balaraman E, Kumar KP. Chem. Rev. 2009; 109: 2551
• 10b Hughes DL. Org. Prep. Proced. Int. 1996; 28: 127
• 10c Mitsunobu O. Synthesis 1981; 1
• 11a Kan T, Fukuyama T. Chem. Commun. 2004; 353
• 11b Fukuyama T, Cheung M, Kan T. Synlett 1999; 1301
• 12a Hagiya K, Muramoto N, Misaki T, Sugimura T. Tetrahedron 2009; 65: 6109
• 12b Sugimura T, Hagiya K. Chem. Lett. 2007; 36: 566
• 13a Xiao Z.-P, Wnag Y.-C, Du G.-Y, Wu J, Luo T, Yi S.-F. Synth. Commun. 2010; 40: 661
• 13b Ramadas K, Srinivasan N. Synth. Commun. 1992; 22: 3189
• 14a Pérez-Serrano L, Domínguez G, Pérez-Castells J. J. Org. Chem. 2004; 69: 5413
• 14b Marco-Contelles J, de Opazo E. J. Carbohydr. Chem. 2002; 21: 201
• 14c Pérez-Serrano L, Casarrubios L, Domínguez G, Pérez-Castells J. Chem. Commun. 2001; 2602
• 14d Ahmar M, Locatelli C, Colombier D, Cazes B. Tetrahedron Lett. 1997; 38: 5281
• 14e Shibata T, Koga Y, Narasaka K. Bull. Chem. Soc. Jpn. 1995; 68: 911
• 15 Gleiter R, Hopf H. Modern Cyclophane Chemistry . Wiley-VCH; Weinheim: 2006: 1