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Volumn , Issue 6, 2008, Pages 831-836

Stereoselective synthesis of a lactam analogue of brefeldin C

(2) Förster, Sebastian a Helmchen, Günter a

Author keywords

Brefeldin C; Iridium catalyzed allylic substitution; Julia Kocie ski olefination; Nozaki Hiyama Kishi reaction; Ring closing metathesis

Indexed keywords

ALLYL COMPOUND; BREFELDIN C; IRIDIUM; LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 42149126132 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042899 Document Type: Article

Times cited : (22)

References (41)

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13
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14
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- this article contains an extensive bibliography of previous total syntheses of Brefeldin A
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15
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- Latest total synthesis: Archambaud, S.; Aphecetche-Julienne, K.; Guingant, A. Synlett 2005, 139.
- (a) Latest total synthesis: Archambaud, S.; Aphecetche-Julienne, K.; Guingant, A. Synlett 2005, 139.

16
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- (b) First total synthesis: Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198.

17
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- Hübscher, T.; Helmchen, G. Synlett 2006, 1323.
- (2006) Synlett , pp. 1323
- Hübscher, T.¹ Helmchen, G.²

18
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- (2005) Chem. Commun , pp. 2957
- Streiff, S.¹ Welter, C.² Schelwies, M.³ Lipowsky, G.⁴ Miller, N.⁵ Helmchen, G.⁶

19
- 42149098521
- 2O <30 mg/L, Karl Fischer titration) and the solution was stirred for 5 min (L2) or 1.5 h (L1). TBD is hygroscopic and was dried under vacuum in a Schlenk tube and stored under argon. For preparation of the ligands see: (a) L1:van Zijl, A. W.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Adv. Synth. Catal. 2004, 326, 413; supporting information,
- 2O <30 mg/L, Karl Fischer titration) and the solution was stirred for 5 min (L2) or 1.5 h (L1). TBD is hygroscopic and was dried under vacuum in a Schlenk tube and stored under argon. For preparation of the ligands see: (a) L1:van Zijl, A. W.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Adv. Synth. Catal. 2004, 326, 413; supporting information,

20
- 17844408116
- L2: Polet, D.; Alexakis, A. Org. Lett. 2005, 7, 1621; supporting information.
- (b) L2: Polet, D.; Alexakis, A. Org. Lett. 2005, 7, 1621; supporting information.

21
- 33947728054
- Gnamm, C.; Förster, S.; Miller, N.; Brödner, K.; Helmchen, G. Synlett 2007, 790.
- (2007) Synlett , pp. 790
- Gnamm, C.¹ Förster, S.² Miller, N.³ Brödner, K.⁴ Helmchen, G.⁵

22
- 42149180954
- Methyl(3R)-2-Cyano-3, trityloxy)methyl]pent-4-enoate (3, A solution of the catalyst in anhyd THF (20 mL) was prepared according to the general procedure from [Ir(cod)Cl]2 (268 mg, 0.40 mmol, L1 (432 mg, 0.80 mmol) and TBD (222 mg, 1.60 mmol, Carbonate 2 (15.54 g, 40.0 mmol, the pronucleophile (5.11 g, 51.6 mmol) and anhyd THF (60 mL) were added, and the solution was stirred at 40°C. Conversion as well as the ratio of branched and linear product were determined by GC. After 60 h the solvent was removed under reduced pressure, and the residue was subjected to flash column chromatography on silica gel (PE-EtOAc, 20:1) to yield 3 (70, as a pale yellow oil which was an inseparable mixture of epimers. Their ratio was determined by 1H NMR (64:36, 1H NMR (300.13 MHz, CDCl3, major epimer, δ, 2.90-3.09 (m, 1 H, CHCH 2, 3.17-3.40 (m, 2 H, CH2O, 3.75 s, 3 H, OMe, 4.1
- 3: C, 78.81; H, 6.12; N, 3.40. Found: C, 78.83; H, 6.32; N, 3.28.

23
- 42149180957
- R[(-)-1S, 2R)-5] = 32 mm.
- R[(-)-1S, 2R)-5] = 32 mm.

24
- 42149098522
- Analytical Data for (1R,2R)-2, Trityloxy)methyl]cyclopentanecarbaldehyde (6, α]D 20 -8.9 (c, 0.525, CHCl3, 1H NMR (300.13 MHz, CDCl3, δ, 1.24-1.38 (m, 1 H, 3-H, 1.50-1.62 (m, 2 H, 4-H, 1.63-1.91 (m, 3 H, 3-H, 5-H, 2.39-2.58 (m, 2 H, 1-H, 2-H, 2.97 (dd, J, 8.2, 8.2 Hz, 1 H, CH2O, 3.19 (dd, J, 5.5, 8.9 Hz, 1 H, CH2O, 7.17-7.45 (m, 15 H, ArH, 9.70 (d, J, 2.3 Hz, 1 H, CHO, 13C NMR (75.48 MHz, CDCl3, δ, 25.09 (t, C-4, 26.78 (t, C-5, 29.68 (t, C-3, 41.78 (d, C-2, 55.85 (d, C-1, 66.58 (t, CH2OCPh3, 86,81 (s, CPh3, 127.07, 127.90, 128.81 (3 x d, CAr, 144.24 (s, CAr, 203.86 (s, CHO, HRMS FAB , m/z [M, Na, calcd for C26H 26O2Na: 393.1831; found: 393.1839
- 2Na: 393.1831; found: 393.1839.

25
- 42149101854
- R[(+)- (S)-3′] = 20 min.
- R[(+)- (S)-3′] = 20 min.

26
- 42149180938
- tert-Butyl Formyl(1-methylprop-2-en-1-yl)carbamate, S)-9, A solution of the catalyst in anhyd THF (1 mL) was prepared according to the general procedure from [Ir(cod)Cl]2 (13.4 mg, 0.01 mmol, R,R,R)-L2 (24.0 mg, 0.02 mmol) and TBD (11.1 mg, 0.40 mmol, Carbonate 7 (265 mg, 2.0 mmol) and Boc(CHO)NH (8; 477 mg, 2.2 mmol) were added, and the solution was stirred for 1.5 h at r.t. The solvent was removed under reduced pressure, and the ratio of branched and linear product was determined by 1H NMR. Flash column chromatography on silica gel (PE-EtOAc, 20:1) afforded pure, S)-9 (85, as a colorless oil; [α]D20 -36.9 [c, 1.08, CHCl3, 96% ee determined by chiral Chrompack permethyl-β- cyclodextrin 25 m x 0.25 mm, temperature program: gradient 4°C/min: 50-90°C, injector temperature 200°C, tR, S
- 3: C, 60.28; H, 8.60; N, 7.03. Found: C, 60.00; H, 8.54; N, 7.13. This preparation was also carried out on a 77-mmol scale with 1 mol% of L1 as ligand to give 9 with 94% ee, branched/linear = 98:2. Amide 10 was obtained after saponification in 81% yield over two steps.

27
- 33748639706
- Weihofen, R.; Tverskoy, O.; Helmchen, G. Angew. Chem. Int. Ed. 2006, 45, 5546;
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 5546
- Weihofen, R.¹ Tverskoy, O.² Helmchen, G.³

28
- 34250840826
- Angew. Chem. 2006, 118, 5673.
- (2006) Angew. Chem , vol.118 , pp. 5673

29
- 0021933679
- We used a simplified version of a method described in: Ziegler, F. E, Klein, S. I, Pati, U. K, Wang, T. F. J. Am. Chem. Soc. 1985, 107, 2730
- We used a simplified version of a method described in: Ziegler, F. E.; Klein, S. I.; Pati, U. K.; Wang, T. F. J. Am. Chem. Soc. 1985, 107, 2730.

30
- 0032817859
- Blakemore, P. R.; Kocieński, P. J.; Marczak, S.; Wicha, J. Synthesis 1999, 1209.
- (1999) Synthesis , pp. 1209
- Blakemore, P.R.¹ Kocieński, P.J.² Marczak, S.³ Wicha, J.⁴

31
- 42149194748
- Preparation of 14: A solution of KHMDS in toluene (0.5 M, 5.6 mL) was added dropwise to a cooled solution, 78°C) of 12 (1.188 g, 2.907 mmol) in DME (11 mL, freshly dried over sodium, containing 70 μg H 2OAnL DME, Karl Fischer titration, After 35 min a solution of 6 (821 mg, 2.216 mmol) in DME (11 mL) was added dropwise. After 3 h at -78°C the solution was allowed to warm to r.t. and was stirred for 60 min. Then H2O (10 mL) and brine (10 mL) were added and the mixture was extracted with Et2O (3 x 20 mL, The combined organic layers were dried over Na2SO4, filtered, and the solvent was evaporated in vacuo. The residue was subjected to flash column chromatography on silica gel (PE-EtOAc, 10:1) to give 14 (1.030 g, 83, as a colorless oil; [α]D20 -19.5 (c, 1.33, CHCl 3, 1H NMR (500.13 MHz, CDCl3, δ, 1.06 d, J
- +].

32
- 85026880256
- The ester 17 was prepared by cis-selective addition of HI to propargylic acid and esterification, cf.: Dixon, J. D.; Ley, S. V.; Longbottom, A. D. Org. Synth. 2003, 80, 129.
- The ester 17 was prepared by cis-selective addition of HI to propargylic acid and esterification, cf.: Dixon, J. D.; Ley, S. V.; Longbottom, A. D. Org. Synth. 2003, 80, 129.

33
- 42149112664
- Preparation of 16: Under an atmosphere of argon, CrCl2 (573 mg, 4.68 mmol) was added to a mixture of 15 (362 mg, 1.17 mmol, methyl (2E)-3-iodoacrylate (17; 495 mg, 2.34 mmol) and NiCl 2 (2.6 mg, 0.012 mmol) in anhyd THF (5 mL) at r.t. After stirring the brownish suspension for 1 h TLC monitoring showed complete conversion. The mixture was treated with H2O and filtered through a pad of silica gel, which was washed with Et2O. The solvent was evaporated in vacuo and the residue was subjected to flash chromatography on silica gel (PE-EtOAc, 9:1) to yield 16 (338 mg, 72, as a colorless oil. NMR data of the major diastereoisomer 16b
- 3N: 295.2147; found: 295.2106.

34
- 12344259557
- In principle, the side chains can be introduced in reversed order, because of a hidden symmetry of 6. However, the NHK reaction with aldehyde 6 proceeded with poor diastereoselectivity of 2:1. Various experiments to effect a reagent-controlled reaction using Kishi's method failed: Namba, K.; Kishi, Y. Org. Lett. 2004, 6, 5031.
- In principle, the side chains can be introduced in reversed order, because of a hidden symmetry of 6. However, the NHK reaction with aldehyde 6 proceeded with poor diastereoselectivity of 2:1. Various experiments to effect a reagent-controlled reaction using Kishi's method failed: Namba, K.; Kishi, Y. Org. Lett. 2004, 6, 5031.

35
- 0000172194
- Helmchen, G. Tetrahedron Lett. 1974, 1527.
- (1974) Tetrahedron Lett , pp. 1527
- Helmchen, G.¹

36
- 42149095762
- Preparation of, -1b: A solution of 16 (338 mg, 0.86 mmol) in THF (7 mL) was treated with an aqueous solution of LiOH (1 M, 7 mL, After stirring for 24 h at r.t. HCl (1 M, 10 mL) and EtOAc (10 mL) were added. The aqueous layer was separated and extracted with EtOAc (3 x 10 mL, The combined organic layers were dried over NaSO4, filtered and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (9 mL) and TFA (2 mL) was added. After stirring for 1 h at r.t. the volatile components were removed in vacuo. A solution of the residue in MeOH-H 2O (10:1) was filtered through a column of the strongly acidic ion-exchange resin Dowex 50 W X 8 (10 g, The column was eluted with a solution of NH3 (0.2-2 M) in MeOH-H2O (10:1) to yield 18 as a white microcrystalline powder (194 mg, 80, Under argon EDCI (310 mg, 1.62 mmol) and HOBt, 122 mg, 0.91 mmol) were added to a cooled (0°C) suspension
- 23ON: 245.1780; found: 245.1788.

37
- 0002339617
- (a) Corey, E. J.; Wollenberg, R. H. Tetrahedron Lett. 1976, 4705.
- (1976) Tetrahedron Lett , pp. 4705
- Corey, E.J.¹ Wollenberg, R.H.²

38
- 0017849778
- (b) Bartlett, P. A.; Green, F. R. J. Am. Chem. Soc. 1978, 100, 4858.
- (1978) J. Am. Chem. Soc , vol.100 , pp. 4858
- Bartlett, P.A.¹ Green, F.R.²

39
- 42149122463
- Preparation of, )-19: Mesyl chloride (142 μL, 1.82 mmol) was added dropwise to a solution of 1b (80 mg, 0.30 mmol, Et3N (253 μL, 1.82 mmol) and DMAP (37 mg, 0.30 mmol) in pyridine (10 mL) at 0°C. The bright orange solution was stirred for 0.5 h at this temperature. Then H2O (10 μL) was added, and the mixture was allowed to warm to r.t. After stirring for 10 min the solution was diluted with EtOAc (10 mL) and a sat. aq solution of CuSO4 (10 mL) was added. The aqueous layer was separated and extracted with EtOAc (3 x 10 mL, The combined organic layers were washed with a sat. aq solution of NaHCO3 (20 mL, dried over Na 2SO4, filtered, and the solvent was removed under reduced pressure. A mixture of the residue with DMF (10 mL) and CsOAc (350 mg, 1.82 mmol) was heated at 80°C. After 19 h, brine and EtOAc were added. The aqueous layer was separated and extracted with EtOAc 3 x 10 mL, The c
- 24ON: 246.1858; found: 246.1867.

40
- 42149180979
- A Mitsunobu reaction with 1b failed to give a useful result.
- A Mitsunobu reaction with 1b failed to give a useful result.

41
- 42149169490
- Analytical Data for, )-1a: [α]D20 -20.1 (c, 0.165, MeOH, 1H NMR (500.13 MHz, CD 3OD, δ, 0.97-1.08 (m, 1 H, 13-H or 7-H, 1.15 (d, J, 6.8 Hz, 3 H, Me, 1.21-1.45 (m, 2 H, 8-H, 14-H, 1.45-1.71 (m, 4 H, 6-H, 13-H2 or 7-H2, 5-H, 1.71-1.86 (m, 5 H, 8-H, 12-H, 14-H, 13-H or 7-H, OH, 1.92-2.05 (m, 2 H, 6-H, 12-H, 2.20 (mc, 1 H, 9-H, 3.87-3.96 (m, 2 H, 4-H, 15-H, 5.16 (dd, J, 9.6, 15.2 Hz, 1 H, 10-H, 5.64 (ddd, J, 4.2, 10.7, 15.0 Hz, 1 H, 11-H, 5.91 (dd, J, 1.1, 16.1 Hz, 1 H, 2-H, 6.63 (dd, J, 5.9, 16.1 Hz, 1 H, 3-H, 13C NMR (125.75 MHz, CD3OD, δ, 21.26 (q, Me, 25.95 (t, C-7 or C-13, 27.70 (t, C-7 or C-13, 32.49 (t, C-6, 33.79 (t, C-12, 36.78 (t, C-8, 37.55 (t, C-14, 47.55 (d, C-15, 48.69 (d, C-9, 53.76 (d, C-5, 77.80 (d, C-4, 123.58 (d, C-1, 131.33 (d, C-11, 137.88 (d, C-10, 147.44 d, C-3, 17
- 23ON: 245.1780; found: 245.1785.

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