Synthesis of Cyclohexane-Angularly-Fused Triquinanes

Dedicated with great affection, admiration and gratitude to Professor Madeleine M. Joullié, who has inspired generations of synthetic chemists with her passion for science, her intellectual rigor and her warmth and humor.

Abstract

Cyclohexane-angularly-fused triquinanes, 6-5-5-5 tetra­cycles, have attracted the attention of synthetic chemists due to their highly congested core structures and multiple quaternary carbon centers. This review focuses on the six completed total synthesis of naturally occurring cyclohexane-angularly-fused triquinanes in addition to seven notable methodologies that have been developed for the synthesis of these structures.

1 Introduction

2 6-5-5-5 Tetracycles Containing a Linear Triquinane

2.1 Total Synthesis of Cyclopiane Diterpenes

2.2 Synthetic Approach toward Aberrarane Diterpenes

2.3 Intermediates in the Total Synthesis of Magellanine-Type Alkaloids

3 6-5-5-5 Tetracycles Containing an Angular Triquinane

3.1 Total Synthesis of Waihoensene

3.2 Miscellaneous Approaches

4 Conclusion

Key words

cyclohexane-angularly-fused triquinane - 6-5-5-5 tetra­cycles - natural products - total synthesis - cyclopianes - waihoensene

Publication History

Received: 16 July 2020

Accepted after revision: 24 August 2020

Article published online:
03 November 2020

• References

• 1a Mehta G, Srikrishna A. Chem. Rev. 1997; 97: 671
• 1b Paquette LA. Top. Curr. Chem. 1984; 119: 1
• 1c Paquette LA. Top. Curr. Chem. 1979; 79: 41
• 2 Comer FW, Trotter J. J. Chem. Soc. B 1966; 11

For recent isolation of unique naturally occurring polyquinanes, see:
• 3a Liu M, Sun W, Shen L, He Y, Liu J, Wang J, Hu Z, Zhang Y. Angew. Chem. Int. Ed. 2019; 58: 12091
• 3b Zhu G.-Y, Yang J, Yao X.-J, Yang X, Fu J, Liu X, Bai L.-P, Liu L, Jiang Z.-H. J. Org. Chem. 2018; 83: 2376
• 4a Qiu Y, Lan W.-J, Li H.-J, Chen L.-P. Molecules 2018; 23: 2095
• 4b Singh V, Thomas B. Tetrahedron 1998; 54: 3647
• 5 Dilmaç AM, Wezeman T, Bär RM, Bräse S. Nat. Prod. Rep. 2020; 37: 224
• 6a Roncal T, Cordobés S, Ugalde U, He Y, Sterner O. Tetrahedron Lett. 2002; 43: 6799
• 6b Roncal T, Cordobés S, Sterner O, Ugalde U. Eukaryot. Cell 2002; 1: 823
• 7a Du L, Li D, Zhu T, Cai S, Wang F, Xiao X, Gu Q. Tetrahedron 2009; 65: 1033
• 7b Gao S.-S, Li X.-M, Zhang Y, Li C.-S, Wang B.-G. Chem. Biodiversity 2011; 8: 1748
• 7c Gao S.-S, Shang Z, Li X.-M, Li C.-S, Cui C.-M, Wang B.-G. Biosci. Biotechnol. Biochem. 2012; 76: 358
• 7d Niu S, Fan Z.-W, Xie C.-L, Liu Q, Luo Z.-H, Liu G, Yang X.-W. J. Nat. Prod. 2017; 80: 2174
• 7e Niu S, Fan Z, Tang X, Liu Q, Shao Z, Liu G, Yang X.-W. Tetrahedron Lett. 2018; 59: 375
• 7f Cheng Z, Li Y, Xu W, Liu W, Liu L, Zhu D, Kang Y, Luo Z, Li Q. Bioorg. Chem. 2019; 91: 103129
• 7g Chen H.-Y, Liu T.-K, Shi Q, Yang X.-L. Fitoterapia 2019; 137: 104243
• 7h Li F, Sun W, Zhang S, Gao W, Lin S, Yang B, Chai C, Li H, Wang J, Hu Z, Zhang Y. Chin. Chem. Lett. 2020; 31: 197
• 8 Shiina T, Nakagawa K, Fujisaki Y, Ozaki T, Liu C, Toyomasu T, Hashimoto M, Koshino H, Minami A, Kawaide H, Oikawa H. Biosci. Biotechnol. Biochem. 2019; 83: 192
• 9 Hou S.-H, Tu Y.-Q, Wang S.-H, Xi C.-C, Zhang F.-M, Wang S.-H, Li Y.-T, Liu L. Angew. Chem. Int. Ed. 2016; 55: 4456
• 10 Hu P, Chi HM, DeBacker KC, Gong X, Keim JH, Hsu IT, Snyder SA. Nature 2019; 569: 705
• 11 Xu B, Xun W, Su S, Zhai H. Angew. Chem. Int. Ed. 2020; 59: 16475
• 12 Henderson JR, Parvez M, Keay BA. Org. Lett. 2007; 9: 5167
• 13 Langer K, Mattay J. J. Org. Chem. 1995; 60: 7256
• 14a Markó I, Ronsmans B, Hesbain-Frisque A.-M, Dumas S, Ghosez L, Ernst B, Greuter H. J. Am. Chem. Soc. 1985; 107: 2192
• 14b Chen L.-Y, Ghosez L. Tetrahedron Lett. 1990; 31: 4467

For a review on keteniminium ions, see:
• 14c Evano G, Lecomte M, Thilmany P, Theunissen C. Synthesis 2017; 49: 3183
• 15 (1S,4R)-Camphanoyl chloride was used as a chiral auxiliary.
• 16 Jiao Z.-W, Tu Y.-Q, Zhang Q, Liu W.-X, Zhang S.-Y, Wang S.-H, Zhang F.-M, Jiang S. Nat. Commun. 2015; 6: 7332
• 17 Brown MK, Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 12904
• 18 Nicolaou KC, Gray DL. F, Montagnon T, Harrison ST. Angew. Chem. Int. Ed. 2002; 41: 996
• 19 Lo JC, Yabe Y, Baran PS. J. Am. Chem. Soc. 2014; 136: 1304
• 20 Corey EJ, Enders D. Tetrahedron Lett. 1976; 17: 3
• 21 Ohshima T, Kagechika L, Adachi M, Sodeoka M, Shibasaki M. J. Am. Chem. Soc. 1996; 118: 7108
• 22 Tian Q, Zhang G. Synthesis 2016; 48: 4038
• 23 Baran PS, Maimone TJ, Richter JM. Nature 2007; 446: 404
• 24 Danheiser RL, Carini DJ, Basak A. J. Am. Chem. Soc. 1981; 103: 1604
• 25a Saborit GV, Cativiela C, Jiménez AI, Bonjoch J, Bradshaw B. Beilstein J. Org. Chem. 2018; 14: 2597
• 25b Friese JC, Krause S, Schäfer HJ. Tetrahedron Lett. 2002; 43: 2683
• 26a Millar JG, Midland SL. Tetrahedron Lett. 2007; 48: 6377
• 26b Schwartz KD, White JD. Org. Synth. 2006; 83: 49
• 27a Oldenziel OH, van Leusen AM. Tetrahedron Lett. 1973; 14: 1357
• 27b Oldenziel OH, van Leusen D, van Leusen AM. J. Org. Chem. 1977; 42: 3114
• 28 Turner OJ, Murphy JA, Hirst DJ, Talbot EP. A. Chem. Eur. J. 2018; 24: 18658

For reviews on metal-catalyzed hydrogen atom transfer strategies, see:
• 29a Crossley SW. M, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912
• 29b Hoffmann RW. Chem. Soc. Rev. 2016; 45: 577
• 29c Green SA, Crossley SW. M, Matos JL. M, Vásquez-Céspedes S, Shevick SL, Shenvi RA. Acc. Chem. Res. 2018; 51: 2628
• 30 Grieco PA, Gilman S, Nishizawa M. J. Org. Chem. 1976; 41: 1485
• 31a Jamison TF, Shambayati S, Crowe WE, Schreiber SL. J. Am. Chem. Soc. 1994; 116: 5505
• 31b Jamison TF, Shambayati S, Crowe WE, Schreiber SL. J. Am. Chem. Soc. 1997; 119: 4353
• 32 Unlike in the previously reported paper (ref. 34), we changed the letter order used to indicate the rings of aberrarone in order to more clearly compare it to that of the cyclopiane natural products.
• 33 Rodríguez II, Rodríguez AD, Zhao H. J. Org. Chem. 2009; 74: 7581
• 34 Kobayashi T, Tokumoto K, Tsuchitani Y, Abe H, Ito H. Tetrahedron 2015; 71: 5918

For recent reviews on Lycopodium alkaloids, see:
• 35a Kitajima M, Takayama H. Top. Curr. Chem. 2012; 309: 1
• 35b Hirasawa Y, Kobayashi J, Morita H. Heterocycles 2009; 77: 679
• 36 Castillo M, Loyola LA, Morales G, Singh I, Calvo C, Holland HL, Maclean DB. Can. J. Chem. 1976; 54: 2893

For the total synthesis of magellanine, see:
• 37a McGee P, Bétournay G, Barabé F, Barriault L. Angew. Chem. Int. Ed. 2017; 56: 6280
• 37b Ishizaki M, Niima Y, Hoshino O, Hara H, Takahashi T. Tetrahedron 2005; 61: 4053
• 37c Yen C.-F, Liao C.-C. Angew. Chem. Int. Ed. 2002; 41: 4090
• 37d Lin K.-W, Ananthan B, Tseng S.-F, Yan T.-H. Org. Lett. 2015; 17: 3938
• 37e Jiang S.-Z, Lei T, Wei K, Yang Y.-R. Org. Lett. 2014; 16: 5612
• 37f Kozaka T, Miyakoshi N, Mukai C. J. Org. Chem. 2007; 72: 10147
• 37g Williams JP, St Laurent DR, Friedrich D, Pimard E, Roden BA, Paquette LA. J. Am. Chem. Soc. 1994; 116: 4689
• 37h Hirst GC, Johnson TO. Jr, Overman LE. J. Am. Chem. Soc. 1993; 115: 2992
• 38 For the isolation of magellaninone, see: Loyola LA, Morales G, Castillo M. Phytochemistry 1979; 18: 1721

For the total synthesis of paniculatine, see:
• 39a Liu J, Chen S, Li N, Qiu FG. Adv. Synth. Catal. 2019; 361: 3514
• 39b Sha C.-K, Lee F.-K, Chang C.-J. J. Am. Chem. Soc. 1999; 121: 9875

For the isolation of paniculatine, see:
• 40a Castillo M, Morales G, Loyola LA, Singh I, Calvo C, Holland HL, MacLean DB. Can. J. Chem. 1976; 54: 2900
• 40b Castillo M, Morales G, Loyola LA, Singh I, Calvo C, Holland HL, MacLean DB. Can. J. Chem. 1975; 53: 2513
• 41 Mehta G, Reddy MS. Tetrahedron Lett. 1990; 31: 2039
• 42 Cookson RC, Grundwell E, Hudec J. Chem. Ind. (London) 1958; 1003
• 43 Mehta G, Srikrishna A, Reddy AV, Nair MS. Tetrahedron 1981; 37: 4543
• 44 For a similar example, see: Mehta G, Rao KS. J. Chem. Soc., Chem. Commun. 1987; 1578
• 45a Abraham WD, Bhupathy M, Cohen T. Tetrahedron Lett. 1987; 28: 2203
• 45b Cohen T, Kuhn D, Falck JR. J. Am. Chem. Soc. 1975; 97: 4749
• 46 Overman LE, Velthuisen E. J. Org. Chem. 2006; 71: 1581
• 47 Hsu D.-S, Rao PD, Liao C.-C. Chem. Commun. 1998; 1795
• 48 Givens RS, Oettle WF, Coffin RL, Carlson RG. J. Am. Chem. Soc. 1971; 93: 3957
• 49 Givens RS, Oettle WF. J. Am. Chem. Soc. 1971; 93: 3963

For similar examples of the synthesis of 6-5-5-5 tetracyclic compounds using the ODPM rearrangement, see:
• 50a Behera TK, Jarhad DB, Mobin SM, Singh V. Tetrahedron 2016; 72: 5377
• 50b Singh V, Singh RB, Mobin SM. Tetrahedron 2009; 65: 7969
• 51 Lio C.-C. Pure Appl. Chem. 2005; 77: 1221
• 52a Ito Y, Aoyama H, Saegusa T. J. Am. Chem. Soc. 1980; 102: 4519
• 52b Ito Y, Hirao T, Saegusa T. J. Org. Chem. 1978; 43: 1011

For recent reviews on the Pauson–Khand reaction, see:
• 53a Lindsay DM, Kerr WJ. In Cobalt Catalysis in Organic Synthesis: Methods and Reactions . Hapke M, Hilt G. Wiley-VCH; Weinheim: 2020: 259
• 53b Ricker JD, Geary LM. Top. Catal. 2017; 60: 609
• 54 Mukai C, Kim JS, Sonobe H, Hanaoka M. J. Org. Chem. 1999; 64: 6822
• 55 Sugihara T, Yamada M, Yamaguchi M, Nishizawa M. Synlett 1999; 771
• 56a Ueno Y, Chino K, Watanabe M, Moriya O, Okawara M. J. Am. Chem. Soc. 1982; 104: 5564

For a review, see:
• 56b Salom-Roig XJ, Dénès F, Renaud P. Synthesis 2004; 1903
• 57 Clarke DB, Hinkley SF. R, Weavers RT. Tetrahedron Lett. 1997; 38: 4297
• 58 Büschleb M, Dorich S, Hanessian S, Tao D, Schenthal KB, Overman LE. Angew. Chem. Int. Ed. 2016; 55: 4156
• 59 Lee H, Kang T, Lee H.-Y. Angew. Chem. Int. Ed. 2017; 56: 8254
• 60 For a review on trimethylenemethane diyl mediated tandem cycloaddition reactions, see: Lee H.-Y. Acc. Chem. Res. 2015; 48: 2308
• 61 Kang T, Song SB, Kim W.-Y, Kim BG, Lee H.-Y. J. Am. Chem. Soc. 2014; 136: 10274
• 62 Mori K, Matsui K. Tetrahedron 1966; 22: 879
• 63 Kaufman GM, Smith JA, Vander Stouw GG, Shechter H. J. Am. Chem. Soc. 1965; 87: 935
• 64 Crawford RJ, Cameron DM. J. Am. Chem. Soc. 1966; 88: 2589
• 65a Van Hijfte L, Little RD, Petersen JL, Moeller KD. J. Org. Chem. 1987; 52: 4647
• 65b Lipshutz BH, Parker DA, Kozlowski JA, Nguyen SL. Tetrahedron Lett. 1984; 25: 5959
• 66a Csuk R, Glanzer BI. Tetrahedron 1991; 47: 1655
• 66b Petasis NA, Bzowej EI. J. Am. Chem. Soc. 1990; 112: 6392
• 67 Qu Y, Wang Z, Zhang Z, Zhang W, Huang J, Yang Z. J. Am. Chem. Soc. 2020; 142: 6511
• 68 Bleschke C, Tissot M, Müller D, Alexakis A. Org. Lett. 2013; 15: 2152
• 69a Hosomi A, Sakurai H. J. Am. Chem. Soc. 1977; 99: 1673
• 69b Hosomi A, Sakurai H. Tetrahedron Lett. 1977; 18: 4041
• 70 Hack D, Blumel M, Chauhan P, Philipps AR, Enders D. Chem. Soc. Rev. 2015; 44: 6059
• 71a Gui J, Pan C.-M, Jin Y, Qin T, Lo JC, Lee BJ, Spergel SH, Mertzman ME, Pitts WJ, La Cruz TE, Schmidt MA, Darvatkar N, Natarajan S, Baran PS. Science 2015; 348: 886
• 71b Lo JC, Gui J, Yabe Y, Pan C.-M, Baran PS. Nature 2014; 516: 343
• 72 Peng C, Arya P, Zhou Z, Snyder SA. Angew. Chem. Int. Ed. 2020; 59: 13521
• 73a May TL, Brown MK, Hoveyda AH. Angew. Chem. Int. Ed. 2008; 47: 7358
• 73b Brown MK, May TL, Baxter CA, Hoveyda AH. Angew. Chem. Int. Ed. 2007; 46: 1097
• 74 Krapcho AP, Weimaster JF, Eldridge JM, Jahngen EG. E, Lovey AJ, Stephens WP. J. Org. Chem. 1978; 43: 138
• 75 Iwasaki K, Wan KK, Oppedisano A, Crossley SW. M, Shenvi RA. J. Am. Chem. Soc. 2014; 136: 1300
• 76a Roth GJ, Liepold B, Müller SG, Bestmann HJ. Synlett 2004; 59
• 76b Müller SG, Liepold B, Roth GJ, Bestmann HJ. Synlett 1996; 521
• 76c Ohira S. Synth. Commun. 1989; 19: 561
• 77 Ergüden J.-K, Moore HW. Org. Lett. 1999; 1: 375
• 78 Zhang Y, Zheng T.-L, Cheng F, Dai K.-L, Zhang K, Ma AJ, Zhang F.-M, Zhang X.-M, Wang S.-H, Tu Y.-Q. Chem. Sci. 2020; 11: 3878
• 79 Stephens RD, Castro CE. J. Org. Chem. 1963; 28: 3313
• 80 Zhang W, Collins MR, Mahmood K, Dowd P. Tetrahedron Lett. 1995; 36: 2729