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Synthesis 2021; 53(11): 1931-1942
DOI: 10.1055/a-1348-4242
DOI: 10.1055/a-1348-4242
paper
Synthesis of Polycycles and Oxacycles via Tandem Metathesis of endo-Norbornene Derivatives
We are thankful to the Department of Science and Technology, Ministry of Science and Technology, India (New Delhi) (EMR/2015/002053), and CSIR (New Delhi) (02(0272)/16/EMR-II) for financial support. S.P. and A.F. thanks University Grants Commission (New Delhi) for financial support and the awarding of a SRF. G.D. and G.S.N. thank Indian Institute of Technology Bombay for the award of post-doctoral fellowship. S.K. thanks the Department of Science and Technology, Ministry of Science and Technology, India (New Delhi) for the awarding of a J. C. Bose fellowship (SR/S2/JCB-33/2010).
Abstract
Here, we have demonstrated that the presence of a carbonyl group at C7 position prevents the olefin metathesis of endo-norbornene derivatives due to complexation of the metal alkylidene. Time-dependent NMR studies showed the presence of new proton signals in the metal alkylidene region, which indicate the formation of metal complex with the carbonyl group of the substrate. These observations were further proved by ESI-MS analysis. Whereas computational studies showed that the catalyst was interacting with the C7 carbonyl group and aligned perpendicular to that of norbornene olefin. These endo-keto norbornene derivatives were reduced to hydroxyl derivatives diastereoselectively. Ring-rearrangement metathesis (RRM) of these hydroxyl derivatives, produced the [6/5/6], and [5/6/5] carbo-tricyclic cores of natural products in one step. Whereas the RRM of O-allyl derivatives, delivered the oxa-tricyclic compounds in a single step with excellent yields.
Key words
Grubbs catalyst - 7-hydroxynorbornene - 7-ketonorbornene - olefin metathesis - natural product synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1348-4242.
- Supporting Information
Publication History
Received: 06 January 2021
Accepted after revision: 08 January 2021
Accepted Manuscript online:
08 January 2021
Article published online:
02 February 2021
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References
- 1a Trnka TM, Grubbs RH. Acc. Chem. Res. 2001; 34: 18
- 1b Kotha S, Meshram M, Khedkar P, Benerjee S, Deodhar D. Beilstein J. Org. Chem. 2015; 11: 1833
- 1c Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts. Cossy J, Arseniyadis S, Meyer C. Wiley-VCH; Weinheim: 2010
- 1d Nolan S, Clavier H. Chem. Soc. Rev. 2010; 39: 3305
- 1e Kotha S, Halder S, Brahmachary E. Tetrahedron 2002; 58: 9203
- 1f Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4490
- 1g Kotha S, Krishna NG, Halder S. Org. Biomol. Chem. 2011; 9: 5597
- 2a Sanford MC, Love JA, Grubbs RH. J. Am. Chem. Soc. 2001; 123: 6543
- 2b Cavallo L. J. Am. Chem. Soc. 2002; 124: 8965
- 2c Adlhart C, Chen P. J. Am. Chem. Soc. 2004; 126: 3496
- 2d Nelson DJ, Manzini S, Urbina-Blanco CA, Nolan SP. Chem. Commun. 2014; 50: 10355
- 2e Paredes-Gil K, Jaque P. Catal. Sci. Technol. 2016; 6: 755
- 3a Kotha S, Meshram M, Dommaraju Y. Chem. Rec. 2018; 18: 1613
- 3b Compain P. Adv. Synth. Catal. 2007; 349: 1829
- 3c Woodward CP, Spiccia ND, Jackson WR, Robinson AJ. Chem. Commun. 2011; 47: 779
- 3d Chatterjee AK, Choi T.-L, Sanders DP, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 11360
- 3e Hoye TR, Zhao H. Org. Lett. 1999; 1: 1123
- 3f Choi T.-L, Chatterjee AK, Grubbs RH. Angew. Chem. Int. Ed. 2001; 40: 1277
- 4a La DS, Sattely ES, Ford JG, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2001; 123: 7767
- 4b Veldhuizen JJ. V, Garber SB, Kingsbury JS, Hoveyda AH. J. Am. Chem. Soc. 2002; 124: 4954
- 4c Braun I, Rudroff F, Mihovilovic MD, Bach T. Synthesis 2007; 3896
- 4d Standen PE, Dodia D, Elsegood MR. J, Teat SJ, Kimber MC. Org. Biomol. Chem. 2012; 10: 8669
- 4e Hartung J, Dornan PK, Grubbs RH. J. Am. Chem. Soc. 2014; 136: 13029
- 4f Yasir M, Liu P, Tennie IK, Kilbinger AF. M. Nat. Chem. 2019; 11: 488
- 5a Du L, Risinger AL, Yee SS, Ola AR. B, Zammiello CL, Cichewicz RH, Mooberry SL. J. Nat. Prod. 2019; 82: 583
- 5b Danielsson J, Sun DX, Chen X.-Y, Risinger AL, Mooberry SL, Sorensen EJ. Org. Lett. 2017; 19: 4892
- 5c Li W, Shen L, Bruhn T, Pedpradeb P, Wu J, Bringmann G. Chem. Eur. J. 2016; 22: 11719
- 5d Lv Z, Chen B, Zhang C, Liang G. Chem. Eur. J. 2018; 24: 9773
- 5e Hanson JR, Manickavasagar R, Thangavelu V. J. Chem. Res. 1998; 734
- 6a Gan C, Fan L, Cui J, Huang Y, Jiao Y, Wei W. Steroids 2012; 77: 1061
- 6b Tian HY, Wang L, Zhang XQ, Wang Y, Zhang DM, Jiang RW, Liu Z, Liu JS, Li YL, Ye WC. Chem. Eur. J. 2010; 16: 10989
- 6c Toueg J, Prunet J. Org. Lett. 2008; 10: 45
- 6d Jin S, Nguyen VT, Dang HT, Nguyen DP, Arman HD, Larionov O. J. Am. Chem. Soc. 2017; 139: 11365
- 6e Paquette LA, Romine JL, Lin H.-S, Wright J. J. Am. Chem. Soc. 1990; 112: 9284
- 6f Paquette LA, Gao Z, Ni Z, Smith GF. J. Am. Chem. Soc. 1998; 120: 2543
- 7a Imai A, Lankin DC, Nikolic D, Ahn S, van Breemen RB, Farnsworth NR, McAlpine JB, Chen SN, Pauli GF. J. Nat. Prod. 2016; 79: 541
- 7b Thao NP, Luyen BT. T, Lee JS, Kim JH, Dat NT, Kim YH. J. Nat. Prod. 2017; 80: 1867
- 7c Kang KB, Kim HW, Kim JW, Oh WK, Kim J, Sung SH. J. Nat. Prod. 2017; 80: 1048
- 7d Gan M, Liu M, Liu B, Lin S, Zhang Y, Zi J, Song W, Fei Y, Chen X, Shi J. J. Nat. Prod. 2011; 74: 2431
- 7e Huang C.-Y, Liaw C.-C, Chen B.-W, Chen P.-C, Su J.-H, Sung P.-J, Dai C.-F, Chiang MY, Sheu J.-H. J. Nat. Prod. 2013; 76: 1902
- 8a Eaton PE, Sidhu RS, Langford GE, Cullison DA, Pietruszewski CL. Tetrahedron 1981; 37: 4479
- 8b Mehta G, Yaragorla S. Tetrahedron Lett. 2011; 52: 4485
- 8c Mehta G, Reddy KS. Tetrahedron Lett. 1996; 37: 2289
- 9a Snajdrova R, Braun I, Bach T, Mereiter K, Mihovilovic MD. J. Org. Chem. 2007; 72: 9597
- 9b Mihovilovic MD, Snajdrova R, Winninger A, Rudroff F. Synlett 2005; 2751
- 9c Mieusset J.-L, Bespokoev A, Pacar M, Abraham M, Arion VB, Brinker UH. J. Org. Chem. 2008; 73: 6551
- 10 Khan FA, Parasuraman K. Beilstein J. Org. Chem. 2010; 6: 64
- 11a Kotha S, Pulletikurti S. Synthesis 2019; 51: 3981
- 11b Kotha S, Mesharam M, Aswar VR. Tetrahedron Lett. 2019; 60: 151337
- 11c Nonn M, Benke Z, Fustero S, Fülöp F, Kiss L. Eur. J. Org. Chem. 2019; 5285
- 11d Kiss L, Benke Z, Remete AM, Fülöp F. Chem. Rec. 2020; 20: 1129
- 11e Grela K. Beilstein J. Org. Chem. 2015; 11: 1639
- 11f Bose S, Ghosh M, Ghosh S. J. Org. Chem. 2012; 77: 6345
- 11g Handore KL, Reddy DS. Org. Lett. 2014; 16: 4252
- 12 Fürstner A, Langemann K. J. Am. Chem. Soc. 1997; 119: 9130
- 13a Seizert CA, Bumbu VD, Birman VB. Org. Lett. 2010; 12: 3472
- 13b Holtsclaw J, Koreeda M. Org. Lett. 2004; 6: 3719
- 13c Spencer TA, Popovici-Müller J, van Beusichem B, Viscardi MacMillan C, Lavey CF, Sin JM, Ditchfield R. Tetrahedron 2010; 66: 4441
- 14 Gordon CP, Yamamoto K, Liao W.-C, Allouche F, Andersen RA, Copéret C, Raynaud C, Eisenstein O. ACS Cent. Sci. 2017; 3: 759
- 15a Kim Y, Chen C.-H, Hilty C. Chem. Commun. 2018; 54: 4333
- 15b Haigh DM, Kenwright AM, Khosravi E. Macromolecules 2005; 38: 7571
- 16a Lam JK, Pham HV, Houk KN, Vanderwal CD. J. Am. Chem. Soc. 2013; 135: 17585
- 16b Poater A, Pump E, Vummaleti SV. C, Cavello L. J. Chem. Theory Comput. 2014; 10: 4442
- 17a Clark FR. S, Warkentin J. Can. J. Chem. 1971; 49: 2223
- 17b Mehta G, Khan FA, Lakshmi KA. Tetrahedron Lett. 1992; 33: 7977
- 17c Yadav VK, Singh L. J. Org. Chem. 2005; 70: 692
- 17d Malihi F, Clive DL. J, Chang C.-C. Minaruzzaman J. Org. Chem. 2013; 78: 996
-
18 CCDC (22a) 1976183 and (22e) 1976182 contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures .
- 19 Chou T.-C, Lin G.-H, Yeh Y.-N, Lin K.-J. J. Chin. Chem. Soc. 1997; 44: 477
- 20 Lannoye G, Kotha S, Wherli S, Cook JM. J. Org. Chem. 1988; 53: 2327
- 21a Kotha S, Sreenivasachary N. Bioorg. Med. Chem. Lett. 2000; 10: 1413
- 21b Kotha S, Halder S. Synlett 2010; 337