Unified Synthesis of (–)-Folicanthine and (–)-Ditryptophenaline Enabled by a Room Temperature Nickel-Mediated Reductive Dimerization

Long Luo; Jian-Jian Zhang; Wei-Jian Ling; Yong-Liang Shao; Ya-Wen Wang; Yu Peng

doi:10.1055/s-0033-1339126

Synthesis, Table of Contents

Synthesis 2014; 46(14): 1908-1916
DOI: 10.1055/s-0033-1339126

special topic

Unified Synthesis of (–)-Folicanthine and (–)-Ditryptophenaline Enabled by a Room Temperature Nickel-Mediated Reductive Dimerization

Long Luo

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 Email: pengyu@lzu.edu.cn

,

Jian-Jian Zhang

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 Email: pengyu@lzu.edu.cn

,

Wei-Jian Ling

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 Email: pengyu@lzu.edu.cn

,

Yong-Liang Shao

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 Email: pengyu@lzu.edu.cn

,

Ya-Wen Wang

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 Email: pengyu@lzu.edu.cn

,

Yu Peng*

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China Fax: +86(931)8912586 Email: pengyu@lzu.edu.cn

› Author Affiliations

Abstract

All articles of this category

Abstract

A Ni·Phen-mediated reductive homocoupling of an optically active tertiary bromide has been efficiently achieved after the systematic screen of reaction conditions including ligands. This key step establishes sterically hindered vicinal quaternary stereocenters embedded in natural bispyrrolo[2,3-b]indoline alkaloids, thus enabling to realize the first asymmetric total synthesis of (–)-folicanthine via the detailed investigation of a challenging double decarboxylation. Notably, the concise synthesis of diketopiperazine alkaloid (–)-ditryptophenaline was also completed from the common dimeric intermediate.

Key words

nickel catalysis - reductive homocoupling - dimeric alkaloids - total synthesis - vicinal quaternary stereocenters

Full Text

References

References

1a Everson D, Shrestha R, Weix DJ. J. Am. Chem. Soc. 2010; 132: 920
1b Everson D, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146
1c Wotal AC, Weix DJ. Org. Lett. 2012; 14: 1476
1d Anka-Lufford LL, Prinsell MR, Weix DJ. J. Org. Chem. 2012; 77: 9989
1e Biswas S, Weix DJ. J. Am. Chem. Soc. 2013; 135: 16192

2a Yu X, Yang T, Wang S, Xu H, Gong H. Org. Lett. 2011; 13: 2138
2b Wu F, Lu W, Qian Q, Ren Q, Gong H. Org. Lett. 2012; 14: 3044
2c Yin H, Zhao C, You H, Lin K, Gong H. Chem. Commun. 2012; 48: 7034
2d Wang S, Qian Q, Gong H. Org. Lett. 2012; 14: 3352
2e Dai Y, Wu F, Zang Z, You H, Gong H. Chem. Eur. J. 2012; 18: 808
2f Xu H, Zhao C, Qian Q, Deng W, Gong H. Chem. Sci. 2013; 4: 4022

3 Cherney AH, Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2013; 135: 7442

4a León T, Correa A, Martin R. J. Am. Chem. Soc. 2013; 135: 1221
4b Correa A, León T, Martin R. J. Am. Chem. Soc. 2014; 136: 1062

5a Yan C.-S, Peng Y, Xu X.-B, Wang Y.-W. Chem. Eur. J. 2012; 18: 6039
5b Xu X.-B, Liu J, Zhang J.-J, Wang Y.-W, Peng Y. Org. Lett. 2013; 15: 550
5c Peng Y, Xu X.-B, Xiao J, Wang Y.-W. Chem. Commun. 2014; 50: 472

6a Peng Y, Luo L, Yan C.-S, Zhang J.-J, Wang Y.-W. J. Org. Chem. 2013; 78: 10960 ; and references cited therein
6b After the acceptance of our article, a related Ni/dppBz-catalyzed dimerization for the syntheses of (±)-folicanthine and (±)-chimonanthine appeared, see: Wada M, Murata T, Oikawa H, Oguri H. Org. Biomol. Chem. 2014; 12: 298

7 For the formal synthesis of (–)-folicanthine employing Pd-DAAA, see: Trost BM, Osipov M. Angew. Chem. Int. Ed. 2013; 52: 9176

For the total synthesis of (+)-folicanthine, see:

8a Movassaghi M, Schmidt MA. Angew. Chem. Int. Ed. 2007; 46: 3725
8b Guo C, Song J, Huang J.-Z, Chen P.-H, Luo S.-W, Gong L.-Z. Angew. Chem. Int. Ed. 2012; 51: 1046
8c Mitsunuma H, Shibasaki M, Kanai M, Matsunaga S. Angew. Chem. Int. Ed. 2012; 51: 5217

For the total synthesis of (+)-chimonanthine, see refs. 8a,c and:

8d Overman LE, Larrow JF, Stearns BA, Vance JM. Angew. Chem. Int. Ed. 2000; 39: 213

For the total synthesis of (–)-chimonanthine, see:

8e Overman LE, Paone D V, Stearns BA. J. Am. Chem. Soc. 1999; 121: 7702
8f Xie W, Jiang G, Liu H, Hu J, Pan X, Zhang H, Wan X, Lai Y, Ma D. Angew. Chem. Int. Ed. 2013; 52: 12924

9a Steven A, Overman LE. Angew. Chem. Int. Ed. 2007; 46: 5488
9b Schmidt MA, Movassaghi M. Synlett 2008; 313

10a Anthoni U, Christophersen C, Nielsen PH In Alkaloids: Chemical and Biological Perspectives . Vol. 13. Pelletier SW. Pergamon; London: 1999: 163-236
10b Tadano S, Ishikawa H. Synlett 2014; 25: 157
10c For a review for the construction of DKP, see: Borthwick AD. Chem. Rev. 2012; 112: 3641

11 López CS, Pérez-Balado C, Rodríguez-Graña P, de Lera ÁR. Org. Lett. 2008; 10: 77

For recent reviews on the construction of pyrroloindolines, see:

12a Crich D, Banerjee A. Acc. Chem. Res. 2007; 40: 151
12b Zhang D, Song H, Qin Y. Acc. Chem. Res. 2011; 44: 447
12c Ruiz-Sanchis P, Savina SA, Albericio F, Álvarez M. Chem. Eur. J. 2011; 17: 1388
12d Repka LM, Reisman SE. J. Org. Chem. 2013; 78: 12314

13a Goldup SM, Leigh DA, McBurney RT, McGonigal PR, Plant A. Chem. Sci. 2010; 1: 383
13b Prinsell MR, Everson DA, Weix DJ. Chem. Commun. 2010; 46: 5743

14 For the utilization of this kind of ligands in the nickel-catalyzed conjugate addition of aryl iodides to enones, see ref. 1b and: Shrestha R, Dorn SC. M, Weix DJ. J. Am. Chem. Soc. 2013; 135: 751
15 We also prepared the analogous precursor bearing benzyloxycarbonyl at C2, and found that only 20% of (–)-2 was detected along with 60% of (+)-5 under identical conditions.
16 Depew KM, Marsden SP, Zatorska D, Zatorski A, Bornmann WG, Danishefsky SJ. J. Am. Chem. Soc. 1999; 121: 11953
17 CCDC-990779 [(–)-2] and CCDC-990780 [(–)-3] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

18a Springer JP, Büchi G, Kobbe B, Demain AL, Clardy J. Tetrahedron Lett. 1977; 18: 2403
18b Nakagawa M, Sugumi H, Kodato S, Hino T. Tetrahedron Lett. 1981; 22: 5323
18c Maes CM, Potgieter M, Steyn PS. J. Chem. Soc., Perkin Trans. 1 1986; 861
18d Barrow CJ, Cai P, Snyder JK, Sedlock DM, Sun HH, Cooper R. J. Org. Chem. 1993; 58: 6016

19a Overman LE, Paone DV. J. Am. Chem. Soc. 2001; 123: 9465
19b Movassaghi M, Schmidt MA, Ashenhurst JA. Angew. Chem. Int. Ed. 2008; 47: 1485
19c Tadano S, Mukaeda Y, Ishikawa H. Angew. Chem. Int. Ed. 2013; 52: 7990

20a Eiter K, Svierak O. Monatsh. Chem. 1951; 82: 186
20b Eiter K, Svierak O. Monatsh. Chem. 1952; 83: 1453
20c Hodson HF, Smith GF. J. Chem. Soc. 1957; 1877

21 For the concern about this challenging step, see the footnote on page 3725 in ref. 8a.

22a Barton DH. R, Crich D, Motherwell WB. J. Chem. Soc., Chem. Commun. 1983; 939
22b Barton DH. R, Crich D, Motherwell WB. Tetrahedron 1985; 41: 3901

23 Ballestri M, Chatgilialoglu C, Cardi N, Sommazzi A. Tetrahedron Lett. 1992; 33: 1787

24a Foo K, Newhouse K, Mori I, Takayama H, Baran PS. Angew. Chem. Int. Ed. 2011; 50: 2716
24b See also: Martin SF, Clark CW, Corbett JW. J. Org. Chem. 1995; 60: 3236

25 For the recent utilization of this reagent in a related mono-decarboxylation reaction, see: Lathrop SP, Movassaghi M. Chem. Sci. 2014; 5: 333
26 Zhang Y.-A, Liu Q, Wang C, Jia Y. Org. Lett. 2013; 15: 3662
27 Espejo VR, Rainier JD. J. Am. Chem. Soc. 2008; 130: 12894
28 Ghosh AK, Xu X. Org. Lett. 2004; 6: 2055
29 Prepared by neutralization of the corresponding sodium salt with aq 1 M HCl, see: Zhong P, Guo S.-r, Song C.-s. Synth. Commun. 2004; 34: 247

Supplementary Material

Supporting Information