Synthetic Study towards Strictamine: The Oxidative Coupling Approach

Weiwu Ren; Nicholas Tappin; Qian Wang; Jieping Zhu

doi:10.1055/s-0033-1339472

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(15): 1941-1944
DOI: 10.1055/s-0033-1339472

letter

Synthetic Study towards Strictamine: The Oxidative Coupling Approach

Weiwu Ren

Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland Fax: +41(21)6939740 eMail: jieping.zhu@epfl.ch

,

Nicholas Tappin

Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland Fax: +41(21)6939740 eMail: jieping.zhu@epfl.ch

,

Qian Wang

Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland Fax: +41(21)6939740 eMail: jieping.zhu@epfl.ch

,

Jieping Zhu*

Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland Fax: +41(21)6939740 eMail: jieping.zhu@epfl.ch

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A synthetic approach featuring a key intramolecular oxidative coupling of a dianion for the formation of the C7–C16 bond was exploited aiming at the synthesis of strictamine. Treatment of substituted tetrahydrocarboline with LHMDS at –78 °C followed by iodine at room temperature afforded a tetracyclic compound, a substructure of eburnane-type alkaloid, via the formation of the N_a–C16 bond.

Key words

strictamine - oxidative coupling - indole alkaloid - tetrahydro-β-carboline

Volltext

Referenzen

References and Notes

1a Schnoes HK, Biemann K, Mokry J, Kompis I, Chatterjee A, Ganguli G. J. Org. Chem. 1966; 31: 1641
1b Pousset J.-L, Poisson J, Olivier L, Le Man J, Janot M.-M. C. R. Hebd. Seances Acad. Sci. 1965; 261: 5538

2 Ahmad Y, Fatima K, Rahman A, Occolowitz JL, Solheim BA, Clardy J, Garnick RL, Le Quesne PW. J. Am. Chem. Soc. 1977; 99: 1943

3a Hugel G, Royer D, Men-Olivier LL, Richard B, Jacquier M.-J, Levy J. J. Org. Chem. 1997; 62: 578
3b Ramirez A, Garcia-Rubio S. Curr. Med. Chem. 2003; 10: 1891

4 Scott AI. Acc. Chem. Res. 1970; 3: 151

Closing ring E via formation of C6–C7 bond, see:

5a Dolby LJ, Nelson SJ. J. Org. Chem. 1973; 38: 2882
5b Bennasar M.-L, Zulaica E, López M, Bosch J. Tetrahedron Lett. 1988; 29: 2361
5c Bennasar M.-L, Zulaica E, Ramírez A, Bosch J. J. Org. Chem. 1996; 61: 1239
5d Kawano M, Kiuchi T, Negishi S, Tanaka H, Hoshikawa T, Matsuo J, Ishibashi H. Angew. Chem. Int. Ed. 2013; 52: 906

Closing ring E via formation of C7–C16 bond, see:

5e Dolby LJ, Esfandiabi Z. J. Org. Chem. 1972; 37: 43
5f Koike T, Takayama H, Sakai S.-I. Chem. Pharm. Bull. 1991; 39: 1677
5g Edwankar RV, Edwankar CR, Namjoshi OA, Deschamps JR, Cook JM. J. Nat. Prod. 2012; 75: 181

Closing ring E via formation of C15–C16 bond, see:

5h Komatsu Y, Yoshida K, Ueda H, Tokuyama H. Tetrahedron Lett. 2013; 54: 377

6a Baran PS, Richter JM. J. Am. Chem. Soc. 2004; 126: 7450
6b Baran PS, Richter JM. J. Am. Chem. Soc. 2005; 127: 15394
6c Baran PS, Guerrero CA, Ambhaikar NB, Hafensteiner BD. Angew. Chem. Int. Ed. 2005; 44: 606
6d Baran PS, DeMartino MP. Angew. Chem. Int. Ed. 2006; 45: 7083
6e Baran PS, Ambhaikar NB, Guerrero CA, Hafensteiner BD, Lin DW, Richter JM. ARKIVOC 2006; 310
6f Richter JM, Whitefield BW, Maimone TJ, Lin DW, Castroviejo MP, Baran PS. J. Am. Chem. Soc. 2007; 129: 12857
6g Richter JM, Idhihara Y, Masuda T, Whitefield BW, Llamas T, Pohjakallio A, Baran PS. J. Am. Chem. Soc. 2008; 130: 17938

7a Martin CL, Overman LE, Rohde JM. J. Am. Chem. Soc. 2008; 130: 7568
7b Martin CL, Overman LE, Rohde JM. J. Am. Chem. Soc. 2010; 132: 4894

8a Zuo Z, Xie W, Ma D. J. Am. Chem. Soc. 2010; 132: 13226
8b Zuo Z, Ma D. Angew. Chem. Int. Ed. 2011; 50: 12008
8c Zi W, Xie W, Ma D. J. Am. Chem. Soc. 2012; 134: 9126
8d Fan F, Xie W, Ma D. Org. Lett. 2012; 14: 1405

9 Guo F, Clift MD, Thomson RJ. Eur. J. Org. Chem. 2012; 4881
10 Wenkert E, Wickberg B. J. Am. Chem. Soc. 1965; 87: 1580
11 Diker K, de Maindreville MD, Lévy J. Tetrahedron Lett. 1995; 36: 2497

12a Brooks DW, Lu LD. L, Masamune S. Angew. Chem., Int. Ed. Engl. 1979; 18: 72
12b Gonzalez GI, Zhu J. J. Org. Chem. 1999; 64: 914

13a Johnson F. Chem. Rev. 1968; 68: 375
13b Hoffmann RW. Chem. Rev. 1989; 89: 1841

14 Various oxidants have been screened, including: Cu(II) salts [copper(II) 2-ethylhexanoate, copper(II) chloride, copper(II) 2-pyrazinecarboxylate, copper(II) acetate, copper(II) trifluoromethanesulfonate, copper(II) acetylacetonate, copper(II) trifluoroacetylacetonate], Fe(III) salts {iron(III) chloride, iron(III) acetylacetonate, ferrocenium hexafluorophosphate, [Fe(DMF)₃Cl₂][FeCl₄]}, Mn(III) salts [manganese(III) acetate, manganese(III) acetylacetonate], Co(II) salts [cobalt(II) acetylacetonate, cobalt(II) acetate], silver(I) trifluoromethanesulfonate, palladium(II) acetate, titanium tetrachloride, and ceric ammonium nitrate.
15 Shen L, Zhang M, Wu Y, Qin Y. Angew. Chem. Int. Ed. 2008; 47: 3618
16 Wang L, Prabhudas B, Clive DL. J. J. Am. Chem. Soc. 2009; 131: 6003
17 Yamanaka E, Nakayama K, Yanagishima N, Nagashima K, Yamauchi M, Sakai S. Chem. Pharm. Bull. 1980; 28: 2527

Selected recent examples of oxidative C–N bond formation:

18a Maity S, Zheng N. Angew. Chem. Int. Ed. 2012; 51: 9562
18b Kobayashi Y, Kuroda M, Toba N, Okada M, Tanaka R, Kimachi T. Org. Lett. 2011; 13: 6280
18c Kim HJ, Kim J, Cho SH, Chang S. J. Am. Chem. Soc. 2011; 133: 16382
18d Kantak AA, Potavathri S, Barham RA, Romano KM, DeBoef B. J. Am. Chem. Soc. 2011; 133: 19960
18e West SP, Bisai A, Lim AD, Narayan RR, Sarpong R. J. Am. Chem. Soc. 2009; 131: 11187

19 Procedure for the Preparation of Compound 13 To a solution of methyl malonate 9 (48.0 mg, 0.1 mmol) in THF (1.0 mL, 0.1 M) was added dropwise LHMDS (0.22 mL, 1.0 M in THF, 0.22 mmol) at –78 °C. After 10 min, the reaction mixture was warmed to r.t. and a solution of iodine (52.0 mg, 0.2 mmol) in THF (0.2 mL) was added. The reaction was stirred at r.t. for 10 min, and then quenched with Na₂S₂O₃ (aq). The aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na₂SO₄, and the volatiles were removed in vacuo. The residue was purified by flash column chromatography (CH₂Cl₂–acetone = 150:1) to yield 13 as a yellow foam (32.0 mg, 69%). IR (neat): 2925, 2854, 1739, 1454, 1229, 1159 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.73 (d, J = 8.2 Hz, 2 H), 7.38–7.36 (m, 1 H), 7.29 (d, J = 8.2 Hz, 2 H), 7.13–7.07 (m, 3 H), 4.46 (dd, J = 11.8, 4.2 Hz, 1 H), 3.90 (s, 3 H), 3.76 (ddd, J = 13.4, 4.4, 4.4 Hz, 1 H), 3.61 (s, 3 H), 3.50 (ddd, J = 13.4, 8.8, 3.6 Hz, 1 H), 2.94–2.89 (m, 1 H), 2.75–2.69 (m, 1 H), 2.66–2.61 (m, 1 H), 2.51–2.43 (m, 1 H), 2.41 (s, 3 H), 2.39–2.32 (m, 1 H), 2.04–1.94 (m, 1 H). ¹³C NMR (101 MHz, CDCl₃): δ = 169.5, 168.0, 143.8, 137.9, 136.7, 131.7, 130.1, 127.7, 127.3, 122.4, 120.7, 118.3, 112.6, 109.9, 68.4, 53.7, 53.2, 53.1, 44.7, 32.1, 27.4, 21.7, 21.3. ESI-HRMS: m/z [M + H]⁺ calcd for C₂₅H₂₇N₂O₆S: 483.1590; found: 483.1598.
20 Csákÿ AG, Plumet J. Chem. Soc. Rev. 2001; 30: 313
21 Rathke MW, Lindert A. J. Am. Chem. Soc. 1971; 93: 4605
22 Brocksom TJ, Petragnani N, Rodrigues R, La Scala Teixeira H. Synthesis 1975; 396
23 Schlitter E, Furlenmeier A. Helv. Chim. Acta 1953; 36: 2017
24 Hájíček J. Collect. Czech. Chem. Commun. 2011; 76: 2023

Zusatzmaterial

Supporting Information