Ring-Closing Metathesis Approach to Cage Propellanes Containing Oxepane and Tetrahydrofuran Hybrid System

Abstract

The preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult to prepare by traditional methods. The synthetic sequence described here opens up new routes to higher order polycycles containing heteroatoms without the involvement of protecting groups. Transannular cyclization observed during Grignard addition and the RCM protocol used here may be applicable to generate unknown oxygenated cage systems.

Key words

Claisen rearrangement - cycloaddition - alkene metathesis - oxepane - tetrahydrofuran hybrid molecules - cage heterocycles - poly­cycles

• References


For selected reviews and monographs on cage systems, see:
• 1a Osawa E. Yonemitsu O. Carbocyclic Cage Compounds . VCH; Weinheim: 1992
• 1b Paquette LA. Chem. Rev. 1989; 89: 1051
• 1c Biegasiewicz KF. Griffiths JR. Savage GP. Tsanaktsidis J. Priefer R. Chem. Rev. 2015; 115: 6719
• 1d Olah GA. Cage Hydrocarbons . Wiley; New York: 1990
• 1e Dilmaç AM. Spuling E. de Meijere A. Bräse S. Angew. Chem. Int. Ed. 2017; 56: 5684
• 1f Hopf H. Classics in Hydrocarbon Chemistry . Wiley-VCH; Weinheim: 2000
• 1g Gharpure SJ. Porwal SK. Org. Prep. Proced. Int. 2013; 45: 81
• 1h Vogtle F. Fascinating Molecules in Organic Chemistry. Wiley; Chichester: 1992
• 2a Eaton PE. Or YS. Branca SJ. Shankar BK. Tetrahedron 1986; 42: 1621
• 2b Lim HN. Dong G. Org. Lett. 2016; 18: 1104
• 2c Marchand AP. Aldrichimica Acta 1995; 28: 95
• 2d Kotha S. Cheekatla SR. Chinnam AK. Jain T. Tetrahedron Lett. 2016; 57: 5605
• 3a Ternansky RJ. Balogh DW. Paquette LA. J. Am. Chem. Soc. 1982; 104: 4503
• 3b Kroto HW. Heath JR. O’Brien SC. Curl RF. Smalley RE. Nature 1985; 318: 162
• 3c Chow TJ. Liu LK. Chao YS. J. Chem. Soc., Chem. Commun. 1985; 700
• 3d Fessner W.-D. Sedelmeier G. Spurr PR. Rihs G. Prinzbach H. J. Am. Chem. Soc. 1987; 109: 4626
• 4a Chow TJ. Chiu N.-R. Chen H.-C. Chen C.-Y. Yu W.-S. Cheng Y.-M. Cheng C.-C. Chang C.-P. Chou P.-T. Tetrahedron 2003; 59: 5719
• 4b Melder J.-P. Fritz H. Prinzbach H. Angew. Chem., Int. Ed. Engl. 1989; 28: 300
• 4c Sahu B. Gururaja GN. Kumar T. Chatterjee A. Ganguly B. Mobin SM. Namboothiri IN. N. J. Org. Chem. 2012; 77: 6998
• 4d Wang SC. Tantillo DJ. Org. Biomol. Chem. 2017; 15: 1976
• 5a Cupas CA. Hodakowski L. J. Am. Chem. Soc. 1974; 96: 4668
• 5b Kruger HG. Martins FJ. C. Viljoen AM. J. Org. Chem. 2004; 69: 4863
• 5c Štimac A. Šekutor M. Mlinarić-Majerski K. Frkanec L. Frkanec R. Molecules 2017; 22: 297
• 6 Marchand AP. Advances in Theoretically Interesting Molecules . JAI Press; Greenwich (CT, USA): 1989
• 7a Greenberg A. Liebman JF. Strained Organic Molecules . Academic Press; New York: 1978
• 7b Chow TJ. Wu T.-K. J. Org. Chem. 1988; 53: 1102
• 8a Cristol SJ. Snell RL. J. Am. Chem. Soc. 1954; 76: 5000
• 8b Cole TW. Jr. Mayers CJ. Stock LM. J. Am. Chem. Soc. 1974; 96: 4555
• 9a Chow TJ. Wu TK. J. Org. Chem. 1991; 56: 6833
• 9b Nair MS. Sudhir U. Joly S. Rath NP. Tetrahedron 1999; 55: 7653
• 9c Mehta G. Srikrishna A. Rao KS. Reddy KR. Acharya KA. Puranik VG. Tavale SS. Guru Row TN. J. Org. Chem. 1987; 52: 457
• 10a Marchand AP. Rajapaksa D. Reddy SP. Watson WH. Nagl A. J. Org. Chem. 1989; 54: 5086
• 10b Krow GR. Tetrahedron 1987; 43: 3
• 11a Mehta G. Rao KS. Krishnamurthy N. Srinivas V. Balasubramanian D. Tetrahedron 1989; 45: 2743
• 11b Marchand AP. Huang Z. Chen Z. Hariprakasha HK. Namboothiri IN. N. Brodbelt JS. Reyzer ML. J. Heterocycl. Chem. 2001; 38: 1361
• 11c Williams SM. Brodbelt JS. Marchand AP. Cal D. Mlinarié-Majerski K. Anal. Chem. 2002; 74: 4423
• 11d Levitskaia TG. Moyer BA. Bonnesen PV. Marchand AP. Krishnudu K. Chen Z. Huang Z. Kruger HG. Mckim AS. J. Am. Chem. Soc. 2001; 123: 12099
• 12a Marchand AP. Suri SC. Earlywine AD. Powel DR. Vander Helm D. J. Org. Chem. 1984; 49: 670
• 12b Mehta G. Srikrishna A. Reddy AV. Nair MS. Tetrahedron 1981; 37: 4543
• 12c Griesbeck AG. Chem. Ber. 1990; 123: 549
• 12d Mehta G. Murthy AN. Reddy DS. Reddy AV. J. Am. Chem. Soc. 1986; 108: 3443
• 13a Deshmukh MB. Borse AU. Mahulikar PP. Dalal DS. Org. Process Res. Dev. 2016; 20: 1363
• 13b Wu Q. Tan L. Hang Z. Wang J. Zang Z. Zhu W. RSC Adv. 2015; 5: 93607
• 13c Rajkumar S. Choudhari RS. Chowdhury A. Namboothiri IN. N. Thermochim. Acta 2013; 563: 38
• 13d Zhang M.-X. Eaton PE. Gilardi R. Angew. Chem. Int. Ed. 2000; 39: 401
• 13e Eaton PE. Zhang M.-X. Gilardi R. Gelber N. Iyer S. Surapaneni R. Prop. Explos. Pyrotech. 2002; 27: 1
• 14a Giacalone F. Martín N. Chem. Rev. 2006; 106: 5136
• 14b Lebedeva MA. Chamberlain TW. Khlobystov AN. Chem. Rev. 2015; 115: 11301
• 15a Wlochal J. Davies RD. M. Burton J. Org. Lett. 2014; 16: 4094
• 15b Wang J. Ma C. Balannik V. Pinto LH. Lamb RA. DeGrado WF. ACS. Med. Chem. Lett. 2011; 2: 307
• 15c Joubert J. Geldenhuys WJ. Van der Schyf CJ. Oliver DW. Kruger HG. Govender T. Malan SF. ChemMedChem 2012; 7: 375
• 15d Gunosewoyo H. Guo JL. Bennett MR. Coster MJ. Kassiou M. Bioorg. Med. Chem. Lett. 2008; 18: 3720
• 15e Hao J. Mdzinarishvili A. Abbruscato TJ. Klein J. Geldenhuys WJ. Van der Schyf CJ. Bickel U. Brain Res. 2008; 1196: 113
• 16a Liu J. Obando D. Liao V. Lifa T. Codd R. Eur. J. Med. Chem. 2011; 46: 1949
• 16b Wilkinson SM. Gunosewoyo H. Barron ML. Boucher A. McDonnell M. Turner P. Morrison DE. Bennett MR. McGregor IS. Rendina LM. Kassiou M. ACS Chem. Neurosci. 2014; 5: 335
• 16c Onajole OK. Coovadia Y. Kruger HG. Maguire Pillay M. Govender T. Eur. J. Med. Chem. 2012; 54: 1
• 16d Beinat C. Banister SD. Hoban J. Tsanaktsidis Metaxas A. Windhorst AD. Kassiou M. Bioorg. Med. Chem. Lett. 2014; 24: 828
• 17 Biegasiewicz KF. Ingalsbe ML. StDenis JD. Gleason JL. Ho J. Coote ML. Savage GP. Priefer R. Beilstein J. Org. Chem. 2012; 8: 1814
• 18a Lal S. Mallick L. Rajkumar S. Ommen OP. Reshmi S. Kumbhakarna N. Chowdhury A. Namboothiri IN. N. J. Mater. Chem. A 2015; 3: 22118
• 18b de Meijere A. Redlich S. Frank D. Magull J. Hofmeister A. Menzel H. Konig B. Svoboda J. Angew. Chem. Int. Ed. 2007; 46: 4574
• 19 Vranesic B. Tomasic J. Smerdel S. Kantoci D. Benedetti F. Helv. Chim. Acta 1993; 76: 1752
• 20 Chalmers BA. Xing H. Housten S. Clark C. Ghassabian S. Kuo A. Cao B. Reitsma A. Murray CE. P. Stock JE. Boyle GM. Pierce CJ. Littler SW. Winkler DA. Bernhardt PV. Pasay C. De Voss JJ. McCarthy J. Parsons PG. Walter GH. Smith MT. Cooper HM. Nilsson SK. Tsanaktsidis J. Savage GP. Williams CM. Angew. Chem. Int. Ed. 2016; 55: 3580
• 21 Gleiter R. Karcher M. Angew. Chem., Int. Ed. Engl. 1988; 27: 840
• 22a Giomi D. Nesi R. Turchi S. Mura E. J. Org. Chem. 2000; 65: 360
• 22b Schneider TF. Werz DB. Org. Lett. 2010; 12: 772
• 22c Khan FA. Dwivedi V. Rout B. Tetrahedron Lett. 2007; 48: 207
• 22d Kong N.-C. Zhang Y. Gao S. Lu Y. Zheng Q.-T. Sun Q.-Y. Yang F.-M. Di Y.-T. Hao XJ. Tetrahedron Lett. 2009; 50: 957
• 22e Álvarez C. Peláez R. Medarde M. Tetrahedron 2007; 63: 2132
• 22f Chang M.-Y. Chena S.-T. Chang N.-C. J. Chin. Chem. Soc. 2001; 48: 1153
• 23a Mehta G. Gagliardini V. Schaefer C. Gleiter R. Tetra­hedron Lett. 2003; 44: 9313
• 23b Resende G. Alvarenga ES. Magn. Reson. Chem. 2016; 54: 968
• 23c Khan FA. Parusuraman K. Beilstein J. Org. Chem. 2010; 6: 1
• 24a Lin H.-C. Wu H.-J. Tetrahedron 2000; 56: 341
• 24b Wu H.-J. Tsai S.-H. Chung W.-S. Tetrahedron Lett. 1996; 37: 8209
• 24c Wu H.-J. Chern J.-H. Tetrahedron 1997; 53: 17653
• 25 Suri SC. J. Org. Chem. 1993; 58: 4153
• 26a Coxon JM. Fong ST. McDonald DQ. O’Connell MJ. Steel PJ. Tetrahedron Lett. 1991; 32: 7115
• 26b Cookson RC. Grunwald E. Hill RR. Hudec J. J. Chem. Soc. 1964; 3062
• 26c Barborak JC. Khoury D. Maier WF. Schleyer P. vR. Smith EC. Smith WF. Wyrick C. J. Org. Chem. 1979; 44: 4761
• 26d Martins FJ. C. Viljoen AM. Kruger HG. Joubert JA. Tetrahedron 1993; 49: 9573
• 27 Mehta G. Reddy KR. J. Org. Chem. 1987; 52: 460
• 28a Marchand A. LaRoe WD. Sharma GV. M. Suri SC. Reddy DS. J. Org. Chem. 1986; 51: 1622
• 28b Fessner WD. Prinzbach H. Tetrahedron 1986; 42: 1797
• 29a Prinzbach H. Klaus M. Angew. Chem., Int. Ed. Engl. 1969; 8: 276
• 29b Marchand AP. Reddy GM. Watson WH. Kashyap R. Tetrahedron 1990; 46: 3409
• 30 Mehta G. Rao HS. P. Reddy KR. J. Chem. Soc., Chem. Commun. 1987; 78
• 31a Wu HJ. Wu CY. J. Org. Chem. 1999; 64: 1576
• 31b Lin HC. Wu CY. Wu HJ. J. Chin. Chem. Soc. 1997; 44: 609
• 31c Mehta G. Vidya R. Venkatesan K. Tetrahedron Lett. 1999; 40: 2417
• 31d Wu HJ. Chao CS. Lin CC. J. Org. Chem. 1998; 63: 7687
• 32 Masusai C. Soorukram D. Kuhakarn C. Tuchinda P. Pakawatchai C. Saithong S. Reutrakul V. Pohmakotr M. J. Org. Chem. 2015; 80: 1577
• 33 Gharpure SJ. Porwal SK. Tetrahedron Lett. 2009; 50: 7162
• 34a Mehta G. Vidya R. J. Org. Chem. 2000; 65: 3497
• 34b Geldenhuys WJ. Malan SF. Murugesan T. vander Schyf CJ. Bloomquist JR. Bioorg. Med. Chem. 2004; 12: 1799
• 34c Mdzinarishvili A. Geldenhuys WJ. Abbruscato TJ. Bickel U. Klein J. VanderSchyf CJ. Neurosci. Lett. 2005; 383: 49
• 34d Wu H.-J. Chern J.-H. Wu C.-Y. Tetrahedron 1997; 53: 2401
• 34e Wu H.-J. Lin C.-C. J. Org. Chem. 1996; 61: 3820
• 34f Chao I. Shih JH. Wu H.-J. J. Org. Chem. 2000; 65: 7523
• 34g Marchand AP. Kumar VS. Hariprakasha HK. J. Org. Chem. 2001; 66: 2072
• 34h James B. Suresh E. Nair MS. Synlett 2006; 3479
• 34i Fokin AA. Zhuk TS. Pashenko AE. Dral PO. Gunchenko PA. Dahl JE. P. Carlson RM. K. Koso TV. Serafin M. Schreiner PR. Org. Lett. 2009; 11: 3068
• 34j Marchand AP. Hazlewood A. Huang Z. Vadlakonda SK. Rocha J.-DR. Power TD. Mlinaric-Majerski K. Klaic L. Kragol G. Bryan JC. Struct. Chem. 2003; 14: 279
• 34k Duque MD. Ma C. Torres E. Wang J. Naesens L. Juárez-Jiménez J. Camps P. Luque FJ. DeGrado WF. Lamb RA. Pinto LH. Vázquez S. J. Med. Chem. 2011; 54: 2646
• 34l Onajole OK. Govender K. Govender P. van Helden PD. Kruger HG. Maguire GE. M. Muthusamy K. Pillay M. Wiid I. Govender T. Eur. J. Med. Chem. 2009; 44: 4297
• 34m Govender T. Kruger HG. Makatini M. Onajole OK. Struct. Chem. 2008; 19: 719
• 35 Boyle GA. Govender T. Kruger HG. Maguire GE. M. Tetrahedron: Asymmetry 2004; 15: 2661
• 36a Marchand AP. McKim SA. Kumar KA. Tetrahedron 1998; 54: 13421
• 36b Hayakawa K. Kido K. Kanematsu K. J. Chem. Soc., Chem. Commun. 1986; 268
• 36c Moriarty RM. Rao MS. C. Tuladhar SM. D’Silva C. Williams G. Gilardi R. J. Am. Chem. Soc. 1993; 115: 1194
• 37a Kotha S. Dipak MK. Chem. Eur. J. 2006; 12: 4446
• 37b Kotha S. Seema V. Singh K. Deodhar KD. Tetrahedron Lett. 2010; 51: 2301
• 37c Kotha S. Cheekatla SR. Mandal B. Eur. J. Org. Chem. 2017; 4277
• 38a The Claisen Rearrangement: Methods and Applications . Hiersemann M. Nubbemeyer U. Wiley-VCH; Weinheim: 2007: 591
• 38b Kotha S. Krishna NG. Halder S. Misra S. Org. Biomol. Chem. 2011; 9: 5597
• 38c Martín Castro AM. Chem. Rev. 2004; 104: 2939
• 38d Kotha S. Mandal K. Tetrahedron Lett. 2004; 45: 9603
• 39a Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
• 39b Kotha S. Chavan AS. Goyal D. ACS Comb. Sci. 2015; 17: 253
• 39c Funel J.-A. Abele S. Angew. Chem. Int. Ed. 2013; 52: 3822
• 39d Corey EJ. Angew. Chem. Int. Ed. 2002; 41: 1650
• 40a Poplata S. Tröster A. Zou Y.-Q. Bach T. Chem. Rev. 2016; 116: 9748
• 40b Kärkäs MD. Porco JA. Jr. Stephenson CR. J. Chem. Rev. 2016; 116: 9683
• 40c Xu Y. Conner ML. Brown MK. Angew. Chem. Int. Ed. 2015; 54: 11918
• 41a Grubbs RH. Wenzel AG. Handbook of Metathesis . Vol. 1. Wiley-VCH; Weinheim: 2015
• 41b Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4490
• 41c Prunet J. Angew. Chem. Int. Ed. 2003; 42: 2826
• 41d Kotha S. Lahiri K. Synlett 2007; 2767
• 41e Kotha S. Mandal K. Chem. Asian J. 2009; 4: 354
• 41f Kotha S. Dipak MK. Tetrahedron 2012; 68: 397
• 41g Kotha S. Manivannan E. Sreenivasachary N. Ganesh T. Deb AC. Synlett 1999; 1618
• 41h Kotha S. Chavan AS. Mobin S. J. Org. Chem. 2012; 77: 482
• 42 Fieser LF. Campbell WP. Fry EM. J. Am. Chem. Soc. 1939; 61: 2206
• 43a Amor F. Royo P. Spaniol TP. Okuda J. J. Organomet. Chem. 2000; 604: 126
• 43b Green ML. H. O’Hare D. J. Chem. Soc., Dalton Trans. 1985; 1585
• 44 Kotha S. Cheekatla SR. ChemSelect 2017; 2: 6877
• 45a Richey HG. Grignard Reagents: New Developments . Wiley; Chichester: 2000: 418
• 45b Baker KV. Brown JM. Hughes N. Skarnulis AJ. Sexton A. J. Org. Chem. 1991; 56: 698
• 45c Orchin M. J. Chem. Educ. 1989; 66: 586
• 46a Kotha S. Manivannan E. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2002; 41: 808
• 46b Kotha S. Manivannan E. Sreenivasachary N. J. Chem. Soc., Perkin Trans. 1 1999; 2845
• 47 Scholl M. Ding S. Lee CW. Grubbs RH. Org. Lett. 1999; 1: 953
• 48 CCDC 1573495 (33) contains 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/getstructures. For ORTEPs of product 33, please see the SI file.
• 49 Hoffmann RW. Synthesis 2006; 3541