Formation of medium-ring heterocyclic compounds by two-directional ring-closing metathesis reaction

Titas Biswas

doi:10.52756/ijerr.2021.v26.006

Authors

Titas Biswas Department of Chemistry, Gurudas College, Kolkata 700054, West Bengal, India

DOI:

https://doi.org/10.52756/ijerr.2021.v26.006

Keywords:

Medium ring heterocyclic compounds, two-directional ring-closing metathesis

Abstract

A synthetic method based on the tandem application of two-directional ring-closing metathesis reaction as key-steps has been established for the synthesis of medium ring heterocyclic compounds.

References

Ahmed, A., Ohler, E. and Mulzer, J. (2001). Synthesis of (S)-4-Methyl-3,6-dihydro-2H pyran-2-carbaldehyde by Twodirectional Ring Closing Metathesis: Application to the C27-C15-Fragment of Laulimalide. Synthesis. 2001(13): 2007-2010.

Bassindale, M. J., Hamely, P., Leituer, A. and Harrity, J. P. A. (1999). Spirocycle assembly through selective tandem ring closing metathesis reactions.Tetrahedron Lett. 40: 3247-3250.

Biswas, T. (2020). Synthesis of heterocyclic compounds using ring-closing enyne metathesis reaction. Int. J. Exp. Res. Rev. 22: 20-29.

Blechert, S. and Connon, S. (2003). Recent Developments in Olefin Cross-Metathesis. Angew. Chem. Int. Ed.Engl. 42(17): 1900-1923.

Burke, S. D., Quinn, K. J. and Chen, V. J. (1998). Synthesis of a C(22)−C(34) Halichondrin B Precursor via Ring Opening−Double Ring Closing Metathesis. The Journal of Organic Chemistry. 63(24): 8626-8627.

Chattopadhyay, S. K., Biswas, T. and Maity, S. (2006). Sequential Double Claisen Rearrangement and Two-Directional Ring-Closing Metathesis as a Route to Various Benzofused Bisoxepin and Bisoxocin Derivatives. Synlett. 14: 2211-2214.

Chattopadhyay, S. K., Karmakar, S., Biswas, T., Majumder, K. C., Rahaman, H. and Roy, B. (2007). Formation of medium-ring heterocycles by diene and enyne metathesis. Tetrahedron. 63: 3919-3952.

Choi, T. L. and Grubbs, R. H. (2001). Tandem ring-closing metathesis reaction with a ruthenium catalyst containing a N-heterocyclic ligand. Chem. Commun. 2001: 2648-2649.

Clark, J. S. and Hamelin, O. (2000). Synthesis of Polycyclic Ethers by Two-Directional Double Ring-Closing Metathesis. Angew. Chem. Int. Ed. Engl. 39(2): 372-374.

Clark, J. S., Grainger, D. M., Ehkirch, A. A. C., Blake, A. J. and Wilson, C. (2007). Synthesis of the Fused Polyether Core of Hemibrevetoxin B by Two-Directional Ring-Closing Metathesis. Org. Lett. 9(6): 1033-1036.

Crimmins, M. T. and Choy, A. L. (1999). An Asymmetric Aldol−Ring-Closing Metathesis Strategy for the Enantioselective Construction of Oxygen Heterocycles: An Efficient Approach to the Enantioselective Synthesis of (+)-Laurencin. J. Am. Chem. Soc. 121: 5653-5660.

Edwards, A. S., Wybrow, R. A. J., Johnstone, C., Adams, H. annnd Harrity, J. P. A. (2002). A new approach to functionalised spiropiperidines through tandem RCM and nitrogen-directed reactions.J. Chem. Soc. Chem. Commun. 2002: 1542-1543.

Fu, G. C.n Son Binh, T. N. and Grubbs, R. H. (1993). Catalytic ring-closing metathesis of functionalized dienes by a ruthenium carbene complex. J. Am. Chem. Soc. 115(21): 9856-9857.

Lautens, M. and Haughes, G. (1999). Diastereoselective Ring Closing Metathesis Reactions: Synthesis of Bicyclic Diallylic Alcohols and Ethers. Angew. Chem. Int. Ed. 38(1/2): 129.

Mehta, G. and Nandakumar, J. (2002). Novel tandem ring-opening/ring-closing metathesis reactions of functionalized cyclohexenoids derived from (−)-α-pinene. Tetrahedron Lett. 43(4): 699-702.

Nomura, K. and Schrock, R. R. (1996). Preparation of “Sugar-Coated” Homopolymers and Multiblock ROMP Copolymers. Macromolecules. 29(2): 540-545.

Schmidt, B. and Westhus, M. (2000). Diastereoselectivity in a Ring Closing Metathesis Reaction with a Remote Stereogenic Centre Leading to Quaternary Dihydropyrans. J. Org. Chem. 65(18): 1817-5822.

Wallace, D. J., Cowden, C. J., Kennedes, D. J., Ashwood, M. S. and Dolling, U. H. (2000). Stereoselective double ring closing metathesis reactions in the synthesis of spirocyclic compounds. Tetrahedron Lett. 41: 2027-2029.

Wallace, D. J., Bulger, P. G., Kennedy D. J., Ashwood, M. S., Cottrell, I. F. and Dolling, U.H. (2001). Stereoselective Double Ring Closing Metathesis Reactions in the Synthesis of Spirocyclic Compounds. Synlett. 2001: 357-360.

Wallace, D. J. (2003). Unusual O-conjugate addition reactions of β-ketoesters and 1,3-diketones to ethyl propynoate: applications to the synthesis of furans.Tetrahedron Lett. 44(2003): 2125-2128.

Wybrow, R. A. J., Johnson, L. A., Auffray, B., Moran, W. J., Adams, H. and Harrity, J. P. A. (2002). Unusual macrocyclic spirocycles from tandem metathesis reactions. Tetrahedron Lett. 43: 7851-7854.

Zuercher, W. J., Hashimoto, M. and Grubbs, R. H. (1996). Tandem Ring Opening−Ring Closing Metathesis of Cyclic Olefins. J. Am. Chem. Soc. 118(28): 6634-6640.