2,8-Diheterobicyclo[3.2.1]octane Ring Systems: Natural Occurrence, Synthesis and Properties

Abstract

This account describes the developments on the synthesis and reactivity of functionalized 2,8-diheterobicyclo[3.2.1]octanes. The continued interest in the chemistry of these compounds is mainly due to their abundance in Nature, being at the core of numerous families of biologically active natural products, and also as a result of their versatile reactivity, which makes them very useful building blocks with considerable impact in modern organic synthesis. The present article is aimed toward providing a comprehensive coverage of the literature on these heterocyclic scaffolds, including our own contributions, and has been organized according to the nature of the heteroatom embedded in the 2,8-bicyclo[3.2.1]octane framework.

1 Introduction

2 2,8-Dioxabicyclo[3.2.1]octane Systems

2.1 Natural Products

2.1.1 Marine Origin: Pectenotoxins, Saliniketals

2.1.2 Terrestrial Origin: Fungus (Squalestatins), Plants

2.2 Synthetic Products

3 2-Aza-8-oxabicyclo[3.2.1]octane Systems

3.1 Cyclonucleotides

3.2 Diazaimide Derivatives

3.3 Systems with a 1,3-Oxazepane Core

3.4 2-Aza-8-oxabicyclo[3.2.1]octanes Fused with Aromatic Rings

3.5 Other Bicyclic Systems

4 2-Thia-8-oxabicyclo[3.2.1]octane Systems

4.1 From Sugars

4.2 Compounds for Asymmetric Epoxidation

4.3 Compounds from Photoreactions of Thioketones

5 2-Oxa-8-azabicyclo[3.2.1]octane Systems

5.1 Natural Products: Kopsia Alkaloids

5.2 Synthetic Products

6 2,8-Diazabicyclo[3.2.1]octane Systems

6.1 Natural Products: Albomitomicyn

6.2 Synthetic Products: Epibatidine Analogues

7 2-Thia-8-azabicyclo[3.2.1]octane Systems

7.1 Natural Products: Diketopiperazines

7.2 Synthetic Products

8 Conclusions

Key words

alkaloids - bicyclic compounds - cycloaddition - natural products - imines

• References

• 1a Gaich T, Baran PS. J. Org. Chem. 2010; 75: 4657
• 1b Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 118: 7292
• 1c Nicolaou KC, Vourloumis D, Winssinger N, Baran PS. Angew. Chem. Int. Ed. 2000; 112: 46
• 2a Heidebrecht RW. Jr, Mulrooney C, Austin CP, Barker RH, Beaudoin JA, Cheng KC.-C, Comer E, Dandapani S, Dick J, Duvall JR, Ekland EH, Fidock DA, Fitzgerald MA, Foley M, Guha R, Hinkson P, Kramer M, Lukens AK, Masi D, Marcaurelle LA, Su X.-Z, Thomas CJ, Weïwer M, Wiegand RC, Wirth D, Xia M, Yuan J, Zhao J, Palmer M, Munoz B, Schreiber SL. ACS Med. Chem. Lett. 2012; 3: 112
• 2b Pizzirani D, Kaya T, Clemons PA, Schreiber SL. Org. Lett. 2010; 12: 2822
• 2c Schreiber SL. ChemBioChem 2009; 10: 26
• 2d Schreiber SL. Nature 2009; 153
• 3a Presset M, Coquerel Y, Rodríguez J. Chem. Rev. 2013; 113: 525
• 3b Presset M, Coquerel Y, Rodriguez J. ChemCatChem 2012; 4: 172
• 3c López F, Castedo L, Mascareñas JL. Chem. Eur. J. 2007; 13: 2172
• 3d Filippini MH, Rodriguez J. Chem. Rev. 1999; 99: 27
• 4 Mohammed KA, Hossain CF, Zhang L, Bruick RK, Zhou Y.-D, Nagle DG. J. Nat. Prod. 2004; 67: 2002
• 5 Wearing XZ, Cook JM. Org. Lett. 2002; 4: 4237
• 6a Schindler CS, Carreira EM. Chem. Soc. Rev. 2009; 38: 3222
• 6b Hartung IV, Hoffmann HM. R. Angew. Chem. Int. Ed. 2004; 43: 1934
• 6c Lautens M, Fagnou K, Hiebert S. Acc. Chem. Res. 2003; 36: 48
• 6d Arjona O, Plumet J. Curr. Org. Chem. 2002; 6: 571
• 6e Misske AM, Hoffmann HM. R. Chem. Eur. J. 2000; 6: 3313
• 6f Vogel P, Cossy J, Plumet J, Arjona O. Tetrahedron 1999; 55: 13521
• 7a Zhao W. Chem. Rev. 2010; 110: 1706
• 7b Singh V, Krishna Vikrant UM, Trivedi GK. Tetrahedron 2008; 64: 3405
• 7c Nair V, Suja TD. Tetrahedron 2007; 63: 12247
• 7d Battiste MA, Pelphrey PM, Wright DL. Chem. Eur. J. 2006; 12: 3438
• 7e Chiu P. Pure Appl. Chem. 2005; 77: 1183
• 7f Wender PA, Love JA In Advances in Cycloadditions . Vol. 6. Harmata M. JAI Press; Stamford: 1999: 1-119
• 7g Rigby JH. Tetrahedron 1999; 55: 4521
• 7h Harmata M. Tetrahedron 1997; 53: 6235
• 7i Kappe CO, Murphree SS, Padwa A. Tetrahedron 1997; 53: 14179
• 7j Padwa A, Weingarten MD. Chem. Rev. 1996; 96: 223
• 7k Katritzky AR, Dennis N. Chem. Rev. 1989; 89: 827
• 7l Mann J. Tetrahedron 1986; 42: 4611
• 7m Noyori R, Hayakawa Y. Org. React. 1983; 29: 163
• 7n Hoffmann HM. R. Angew. Chem., Int. Ed. Engl. 1984; 23: 1
• 7o Noyori R. Acc. Chem. Res. 1979; 12: 61
• 8a Song G, Chen D, Su Y, Han K, Pan CL, Jia A, Li X. Angew. Chem. Int. Ed. 2011; 50: 7791
• 8b Jaber DM, Burgin RN, Hepler M, Zavalij P, Doyle MP. Chem. Commun. 2011; 47: 7623
• 8c Ishida K, Kusama H, Iwasawa N. J. Am. Chem. Soc. 2010; 132: 8842
• 8d Trillo B, López F, Gulias M, Castedo L, Mascareñas JL. Angew. Chem. Int. Ed. 2008; 47: 951
• 8e Barluenga J, Diéguez A, Fernández A, Rodríguez F, Fañanás FJ. Angew. Chem. Int. Ed. 2006; 118: 2145
• 8f Kusama H, Funami H, Shido M, Hara Y, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2005; 127: 2709
• 9 Xing S, Pan W, Liu C, Ren J, Wang Z. Angew. Chem. Int. Ed. 2010; 49: 3215
• 10 Hu B, Xing S, Ren J, Wang Z. Tetrahedron 2010; 66: 5671
• 11 Bai Y, Tao W, Ren J, Wang Z. Angew. Chem. Int. Ed. 2012; 51: 4112
• 12a Sasaki K, Wright JL. C, Yasumoto T. J. Org. Chem. 1998; 63: 2475
• 12b Yasumoto T, Murata M. Chem. Rev. 1993; 93: 1897
• 12c Murata M, Sano M, Iwashita T, Naoki H, Yasumoto T. Agric. Biol. Chem. 1986; 50: 2693
• 12d Yasumoto T, Murata M, Oshima Y, Sano M, Matsumoto GK, Clardy J. Tetrahedron 1985; 41: 1019
• 13a Miles CO, Wilkins AL, Hawkes AD, Jensen DJ, Selwood AI, Beuzenberg V, MacKenzie AL, Cooney JM, Holland PT. Toxicon 2006; 48: 152
• 13b Miles CO, Wilkins AL, Samdal IA, Sandvik M, Petersen D, Quillam MA, Naustvoll TR, Rundberget T, Torgersen T, Hovgaard P, Jensen DJ, Cooney JM. Chem. Res. Toxicol. 2004; 17: 1423
• 14a Espiña B, Louzao MC, Ares IR, Fonfría ES, Vilariño N, Vieytes MR, Yasumoto T, Botana LM. Chem. Res. Toxicol. 2010; 23: 504
• 14b Kim G.-Y, Kim W.-J, Choi YH. Mar. Drugs 2011; 9: 2176
• 14c Jung JH, Sim CJ, Lee C.-O. J. Nat. Prod. 1995; 58: 1722
• 15a Evans DA, Rajapakse HA, Stenkamp D. Angew. Chem. Int. Ed. 2002; 41: 4569
• 15b Evans DA, Rajapakse HA, Chiu A, Stenkamp D. Angew. Chem. Int. Ed. 2002; 41: 4573
• 16 Carley S, Brimble MA. Org. Lett. 2009; 11: 563
• 17 Fujiwara K, Suzuki Y, Koseki N, Murata S.-i, Murai A, Kawai H, Suzuki T. Tetrahedron Lett. 2011; 52: 5589
• 18 Canterbury DP, Micalizio GC. Org. Lett. 2011; 13: 2384
• 19 Kubo O, Canterbury DP, Micalizio GC. Org. Lett. 2012; 14: 5748
• 20a Kouridaki A, Montagnon T, Kalaitzakis D, Vassilikogiannakis G. Org. Biomol. Chem. 2013; 11: 537
• 20b Kouridaki A, Montagnon T, Tofi M, Vassilikogiannakis G. Org. Lett. 2012; 14: 2374
• 21a Williams PG, Asolkar RN, Kondratyuk T, Pezzuto JM, Jensen PR, Fenical W. J. Nat. Prod. 2007; 70: 83
• 21b Mincer TJ, Jensen PR, Kauffman CA, Fenical W. Appl. Environ. Microbiol. 2002; 68: 5005
• 22 Paterson I, Razzak M, Anderson EA. Org. Lett. 2008; 10: 3295
• 23 De Brabander JK, Liu J. J. Am. Chem. Soc. 2009; 131: 12562
• 24 Yadav JS, Hossain S, Madhu M, Mohapatra DK. J. Org. Chem. 2009; 74: 8822
• 25a Hasumi K, Tachikawa K, Sakai K, Murakawa S, Yoshikawa N, Kumuzawa S, Endo A. J. Antibiot. 1993; 46: 689
• 25b Dawson MJ, Farthing JE, Marshall PS, Middleton RF, O’Neill MJ, Shuttleworth A, Stylli C, Tait RM, Taylor PM, Wildman HG, Buss AD, Langley D, Hayes MJ. J. Antibiot. 1992; 45: 639
• 25c Baxter A, Fitzgerald BJ, Hutson JL, McCarthy AD, Motteram JM, Ross BL, Sapra M, Snowden MA, Watson NS, Williams RJ, Wright CJ. J. Biol. Chem. 1992; 267: 11705
• 26 Bate C, Salmona M, Diomede L, Williams A. J. Biol. Chem. 2004; 279: 14983
• 27 Li HY, Appelbaum FR, Willman CL, Zager RA, Banker DE. Blood 2003; 101: 3628
• 28 Nadin A, Nicolaou KC. Angew. Chem., Int. Ed. Engl. 1996; 35: 1622
• 29 Armstrong A, Blench TJ. Tetrahedron 2002; 58: 9321
• 30 Nakurama S. Chem. Pharm. Bull. 2005; 53: 1
• 31a Zhang C.-R, Liu H.-B, Feng T, Zhu J.-Y, Geng M.-Y, Yue Y.-M. J. Nat. Prod. 2009; 72: 1669
• 31b Morita H, Kobayashi J. Org. Lett. 2003; 5: 2895
• 31c Morita H, Takatsu H, Kobayashi J. Tetrahedron 2003; 59: 3575
• 32 To Hoai N, Sasaki A, Sasaki M, Kaga H, Kakuchi T, Satoh T. Carbohydr. Res. 2011; 346: 1747
• 33 Giorgi G, López-Alvarado P, Menéndez JC. Org. Biomol. Chem. 2012; 10: 5131
• 34 Vu CS, Guisot N, Guillarme S, Martel A, Dujardin G, Pipelier M, Dubreuil D, Saluzzo C. Eur. J. Org. Chem. 2012; 3727
• 35 Meng J, Zhao Y.-L, Ren C.-Q, Li Y, Li Z, Liu Q. Chem. Eur. J. 2009; 15: 1830
• 36a Aquino M, Safir I, Elkhayat Z, Gandara Z, Pérez M, Retailleau P, Arseniyadis S. Org. Lett. 2009; 11: 3610
• 36b Elkhayat Z, Safir I, Aquino M, Pérez M, Gandara Z, Retailleau P, Arseniyadis S. Eur. J. Org. Chem. 2009; 2687
• 36c Ozturk C, Topal K, Aviyente V, Tuzun N, Sánchez E, Arseniyadis S. J. Org. Chem. 2005; 70: 7080
• 36d Finet L, Candela Lena JI, Kaoudi T, Birlirakis N, Arseniyadis S. Chem. Eur. J. 2003; 9: 3813
• 37 Chanu A, Safir I, Basak R, Chiaroni A, Arseniyadis S. Org. Lett. 2007; 9: 1351
• 38 Elkhayat Z, Safir I, Gandar Z, Retailleau P, Arseniyadis S. Eur. J. Org. Chem. 2010; 4851
• 39 Castillo RR, Aquino M, Gandar Z, Safir I, Elkhayat Z, Retailleau P, Arseniyadis S. Org. Lett. 2012; 14: 1628
• 40 Acharya A, Eickoff JA, Jeffrey CS. Synthesis 2013; 45: 1825
• 41 Nicotra F, Cipolla L, Peri F, La Ferla B, Redaelli C. Adv. Carbohydr. Chem. Biochem. 2007; 61: 353
• 42a Gantt RW, Peltier-Pain P, Thorson JS. Nat. Prod. Rep. 2011; 28: 1811
• 42b Thibodeaux CJ, Melançon CE. III, Liu H.-W. Angew. Chem. Int. Ed. 2008; 47: 9814
• 43 Ueda T. Nucleosides Nucleotides 1985; 4: 67
• 44 Keck K. Z. Naturforsch. B 1968; 23: 1034
• 45 Cadet J, Delatour T, Douki T, Gasparutto D, Pouget JP, Ravanat JL, Sauvaigo S. Mutat. Res. 1999; 424: 9
• 46 Evans MD, Dizdaroglu M, Cooke MS. Mutat. Res. 2004; 567: 1
• 47 Wang J, Clauson CL, Robbins PD, Niedernhofer LJ, Wang Y. Aging Cell 2012; 11: 714
• 48a Jiménez LB, Encinas S, Chatgilialoglu C, Miranda MA. Org. Biomol. Chem. 2008; 6: 1083
• 48b Fabien Boussicault F, Kaloudis P, Caminal C, Mulazzani QG, Chatgilialoglu C. J. Am. Chem. Soc. 2008; 130: 8377
• 48c Chatgilialoglu C, Duca M, Ferreri C, Guerra M, Ioele M, Mulazzani QG, Strittmatter H, Giese B. Chem. Eur. J. 2004; 10: 1249
• 48d Chatgilialoglu C, Guerra M, Mulazzani QG. J. Am. Chem. Soc. 2003; 125: 3839
• 48e Flyunt R, Bazzanini R, Chatgilialoglu C, Mulazzani QG. J. Am. Chem. Soc. 2000; 122: 4225
• 49 Chatgilialoglu C, Gimisis T. Chem. Commun. 1998; 1249
• 50 Terzidis MA, Chatgilialoglu C. Aust. J. Chem. 2013; 66: 330
• 51a Kamakura N, Yamamoto J, Brooks PJ, Iwai S, Kuraoka I. Chem. Res. Toxicol. 2012; 25: 2718
• 51b Brooks PJ. DNA Repair 2008; 7: 1168
• 52 Karwowski BT. Org. Biomol. Chem. 2010; 8: 1603
• 53 Karwowski BT, Gaillard J, Grand A, Cadet J. Org. Biomol. Chem. 2008; 6: 3408
• 54a Muller E, Gasparutto D, Jacquinod M, Romieu A, Cadet J. Tetrahedron 2000; 56: 8689
• 54b Muller E, Gasparutto D, Cadet J. ChemBioChem 2002; 3: 534
• 55 Schulhof JC, Molko D, Teoule R. Nucleic Acids Res. 1987; 15: 397
• 56 Theile CS, McLaughlin LW. Chem. Commun. 2012; 48: 5587
• 57a Yoshimura Y, Yamazaki Y, Wachi K, Satoh S, Takahata H. Synlett 2007; 111
• 57b Ueda T, Usui H, Shuto S, Inoue H. Chem. Pharm. Bull. 1984; 32: 3410
• 57c Otter BA, Falco EA, Fox JJ. J. Org. Chem. 1976; 41: 3133
• 58a Padwa A, Hertzog DL, Chinn RL. Tetrahedron Lett. 1989; 30: 4077
• 58b Padwa A, Dean DC, Hertzog DL, Nadler WR, Zhi L. Tetrahedron 1992; 48: 7565
• 59 Nikolaev VV, Krylov IS, Schulze B, Rodina LL. Russ. J. Org. Chem. 2005; 41: 784
• 60 Enßle M, Buck S, Werz R, Maas G. ARKIVOC 2012; (iii): 149
• 61 Gerster H, Espenlaub S, Maas G. Synthesis 2006; 2251
• 62 Moris-Varas F, Quian X.-H, Wong C.-H. J. Am. Chem. Soc. 1996; 118: 7647
• 63 Paulsen H, Todt K. Chem. Ber. 1967; 100: 512
• 64 Herdeis C, Mohareb RM, Neer RB, Schwabenländer F, Telser J. Tetrahedron: Asymmetry 1999; 10: 4521
• 65 Cid P, Closa M, March P, Figueredo M, Font J, Sanfeliu E, Soria A. Eur. J. Org. Chem. 2004; 20: 4215
• 66 Martínez-Castro E, González-Benjumea A, López O, Maya I, Álvarez E, Fernández-Bolaños JG. Org. Biomol. Chem. 2012; 10: 4220
• 67 Brinson RG, Jones PB. Tetrahedron Lett. 2004; 45: 6155
• 68 Moutrille C, Zard SZ. Tetrahedron Lett. 2004; 45: 4631
• 69 Al Dulayymi AR, Baird MS, Clegg W. Tetrahedron Lett. 1997; 38: 8271
• 70a Gallos JK, Koftis TV. J. Chem. Soc., Perkin Trans. 1 2001; 415
• 70b Gallos JK, Demeroudi SC, Stathopoulou CC, Dellios CC. Tetrahedron Lett. 2001; 42: 7497
• 71 Hashmi AS. K, Bührle M, Wölfle M, Rudolph M, Wieteck M, Rominger F, Frey W. Chem. Eur. J. 2010; 16: 9846
• 72 Whistler RL, Urbas B. J. Org. Chem. 1965; 30: 2721
• 73 Cox JM, Owen LN. J. Chem. Soc. C 1967; 1121
• 74 Shin JE. N, Perlin AS. Carbohydr. Res. 1980; 84: 315
• 75 Hughes NA, Todhunter NT. Carbohydr. Res. 2000; 326: 81
• 76 Bozo E, Demeter A, Rill A, Kuszmann J. Tetrahedron: Asymmetry 2001; 12: 3423
• 77a Berrisford DJ, Bolm C, Sharpless KB. Angew. Chem., Int. Ed. Engl. 1995; 34: 1059
• 77b Jacobsen EN. In Catalytic Asymmetric Synthesis . Ojima I. Wiley-VCH; New York: 1993: 159
• 77c Katsuki T, Martin VS. Org. React. 1996; 48: 1
• 78 Trost BM, Hammen RF. J. Am. Chem. Soc. 1973; 95: 962
• 79 Aggarwal VK, Ford JG, Fonquerna S, Adams H, Jones RV. H, Fieldhouse R. J. Am. Chem. Soc. 1998; 120: 8328
• 80 Aggarwal VK, Angelaud R, Bihan D, Blackburn P, Fieldhouse R, Fonquerna S, Ford JG, Hynd G, Jones E, Jones RV. H, Jubault P, Palmer MJ, Ratcliffe PD, Adams H. J. Chem. Soc., Perkin Trans. 1 2001; 2604
• 81 Nishio T. J. Chem. Soc., Perkin Trans. 1 1995; 561
• 82 Sevenet T, Allorge L, David B, Awang K, Hadi AH. A, Kan-Fan C, Quirion JC, Remy F, Schaller H, Teo LE. J. Ethnopharmacol. 1994; 41: 147
• 83a Kam TS, Yoganathan K, Chen W. J. Nat. Prod. 1996; 59: 1109
• 83b Kam TS, Yoganathan K, Chuah CH. Tetrahedron Lett. 1995; 36: 759
• 83c Kam TS, Yoganathan K, Chuah CH. Tetrahedron Lett. 1994; 35: 4457
• 84 Lim S.-H, Sim K.-M, Abdullah Z, Hiraku O, Hayashi M, Komiyama K, Kam TS. J. Nat. Prod. 2007; 70: 1380
• 85 Kam T.-S, Lim T.-M, Tan G.-H. J. Chem. Soc., Perkin Trans. 1 2001; 1594
• 86 Zanardi F, Battistini L, Nespi M, Rassu G, Spanu P, Cornia M, Casiraghi G. Tetrahedron: Asymmetry 1996; 7: 1167
• 87 Flores MF, García P, Garrido NM, Nieto C, Basabe P, Marcos IS, Sanz F, Goodman JN, Díez D. Tetrahedron: Asymmetry 2012; 23: 76
• 88a Flores MF, García P, Garrido NM, Marcos IS, Sanz F, Díez D. RSC Adv. 2012; 2: 11040
• 88b Hashmi SM. A, Ali SA, Wazeer MI. M. Tetrahedron 1998; 54: 12959
• 89 Chevrier C, Le Nouën D, Defoin A, Tarnus C. Carbohydr. Res. 2011; 346: 1202
• 90a Avendaño C, Menéndez JC. Medicinal Chemistry of Anticancer Drugs . Elsevier; Amsterdam: 2008. Chap. 6
• 90b Wolkenberg SE, Boger DL. Chem. Rev. 2002; 102: 2477
• 90c Franck RW, Tomasz M In The Chemistry of Antitumor Agents . Wilman DE. V. Blackie & Son; Glasgow: 1990: 379
• 90d Doroshow JH. J. Natl. Cancer Inst. 1992; 84: 1138
• 91 Fiallo MM. L, Deydier E, Bracci M, Garnier-Suillerot A, Halvorsen K. J. Med. Chem. 2003; 46: 1683
• 92 Kono M, Saitoh Y, Shirahata K, Arai Y, Ishii S. J. Am. Chem. Soc. 1987; 109: 7224
• 93 Kasai M, Kono M, Ikeda S.-I, Yoda N, Hirayama N. J. Org. Chem. 1992; 57: 7296
• 94 Moreno-Vargas AJ, Vogel P. Tetrahedron Lett. 2003; 44: 5069
• 95a Ding G, Jiang L, Guo L, Chen X, Zhang H, Che Y. J. Nat. Prod. 2008; 71: 1861
• 95b Yamada T, Iwamoto C, Yamagaki N, Yamanouchi T, Minoura K, Yamori T, Uehara Y, Andoh T, Umenura K, Numata A. Tetrahedron 2002; 58: 479
• 95c Kleinwächter P, Dahse H.-M, Luhmann U, Schlegel B, Dornberger K. J. Antibiot. 2001; 54: 521
• 95d Bull SD, Davies SG, Parkin RM, Sancho FS. J. Chem. Soc., Perkin Trans. 1 1998; 231
• 95e Takahashi C, Minoura K, Yamada T, Numata A, Kushida K, Shingu T, Hagishita S, Nakai H, Sato T, Harada H. Tetrahedron 1995; 51: 3483
• 95f Takahashi C, Numata A, Ito Y, Matsumura E, Araki H, Iwaki H, Kushida K. J. Chem. Soc., Perkin Trans. 1 1994; 1859
• 96 Tan RX, Jensen PR, Williams PG, Fenical W. J. Nat. Prod. 2004; 67: 1374
• 97 Deffieux G, Baute MA, Baute R, Filleau MJ. J. Antibiot. 1978; 31: 1102
• 98a Minato H, Matsumoto M, Katayama T. J. Chem. Soc., Perkin Trans. 1 1973; 1819
• 98b Joshi BK, Gloer JB, Wicklow DT. J. Nat. Prod. 1999; 62: 730
• 99a Wang J.-M, Ding G.-Z, Fang L, Dai J.-G, Yu S.-S, Wang Y.-H, Chen X.-G, Ma S.-G, Qu J, Xu S, Du D. J. Nat. Prod. 2010; 73: 1240
• 99b Guo H, Sun B, Gao H, Chen X, Liu S, Yao X, Liu X, Che Y. J. Nat. Prod. 2009; 72: 2115
• 99c Zhang Y, Liu S, Che Y, Liu X. J. Nat. Prod. 2007; 70: 1522
• 100 Nagarajan R, Woody RW. J. Am. Chem. Soc. 1973; 95: 7212
• 101 Wang J.-m, Jiang N, Ma J, Yu S.-s, Tan R.-x, Dai J.-g, Si Y.-k, Ding G.-z, Ma S.-g, Qu J, Fang L, Du D. Tetrahedron 2013; 69: 1195
• 102 Nishio T, Okuda N. J. Org. Chem. 1992; 57: 4000