SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 51, Issue 23, 2012, Pages 5687-5691

Total synthesis of (-)-atrop-abyssomicin C

(2) Bihelovic, Filip a Saicic, Radomir N a

a UNIVERSITY OF BELGRADE (Serbia)

Author keywords

antibiotics; cyclization; gold; natural products; total synthesis

Indexed keywords

DUAL CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; MARINE ANTIBIOTIC; NATURAL PRODUCTS; RING CLOSURES; SYNTHETIC SEQUENCE; TOTAL SYNTHESIS;

ANTIBIOTICS; CYCLIZATION; GOLD;

CATALYSIS;

ABYSSOMICIN C; CYCLOHEXANE; CYCLOHEXANE DERIVATIVE; FUSED HETEROCYCLIC RINGS; GOLD;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; CYCLIZATION; CYCLOHEXANES; GOLD; STEREOISOMERISM;

EID: 84861629455 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201108223 Document Type: Article

Times cited : (57)

References (62)

1
- 13844273541
- B. Bister, D. Bischoff, M. Ströbele, J. Riedlinger, A. Reicke, F. Wolter, A. T. Bull, H. P. Fiedler, R. D. Süssmuth, Angew. Chem. 2004, 116, 2628-2630
- (2004) Angew. Chem. , vol.116 , pp. 2628-2630
- Bister, B.¹ Bischoff, D.² Ströbele, M.³ Riedlinger, J.⁴ Reicke, A.⁵ Wolter, F.⁶ Bull, A.T.⁷ Fiedler, H.P.⁸ Süssmuth, R.D.⁹

2
- 4544291065
- Angew. Chem. Int. Ed. 2004, 43, 2574-2576.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2574-2576

3
- 66449131329
- For a review article on naturally occurring antibiotics, see:, K. C. Nicolaou, J. S. Chen, D. J. Edmonds, A. A. Estrada, Angew. Chem. 2009, 121, 670-732
- (2009) Angew. Chem. , vol.121 , pp. 670-732
- Nicolaou, K.C.¹ Chen, J.S.² Edmonds, D.J.³ Estrada, A.A.⁴

4
- 58249108035
- Angew. Chem. Int. Ed. 2009, 48, 660-719.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 660-719

5
- 2342507638
- J. Riedlinger, A. Riecke, H. Zahner, B. Krismer, A. T. Bull, L. A. Maldonado, A. C. Ward, M. Goodfellow, B. Bister, D. Bischoff, R. D. Süssmuth, H.-P. Fiedler, J. Antibiot. 2004, 57, 271-279
- (2004) J. Antibiot. , vol.57 , pp. 271-279
- Riedlinger, J.¹ Riecke, A.² Zahner, H.³ Krismer, B.⁴ Bull, A.T.⁵ Maldonado, L.A.⁶ Ward, A.C.⁷ Goodfellow, M.⁸ Bister, B.⁹ Bischoff, D.¹⁰ Süssmuth, R.D.¹¹ Fiedler, H.-P.¹²

6
- 42149158322
- S. Keller, H. S. Schadt, I. Ortel, R. D. Süssmuth, Angew. Chem. 2007, 119, 8433-8435
- (2007) Angew. Chem. , vol.119 , pp. 8433-8435
- Keller, S.¹ Schadt, H.S.² Ortel, I.³ Süssmuth, R.D.⁴

7
- 36049020256
- Angew. Chem. Int. Ed. 2007, 46, 8284-8286.
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8284-8286

8
- 34948837927
- S. Keller, G. Nicholson, C. Drahl, E. Sorensen, H.-P. Fiedler, R. D. Süssmuth, J. Antibiot. 2007, 60, 391-394; for Abyssomicin E, see
- (2007) J. Antibiot. , vol.60 , pp. 391-394
- Keller, S.¹ Nicholson, G.² Drahl, C.³ Sorensen, E.⁴ Fiedler, H.-P.⁵ Süssmuth, R.D.⁶

9
- 34547228672
- X. M. Niu, S. H. Li, H. Gorls, D. Schollmeyer, M. Hillinger, S. Grabley, I. Sattler, Org. Lett. 2007, 9, 2437-2440; for Abyssomicin I, see
- (2007) Org. Lett. , vol.9 , pp. 2437-2440
- Niu, X.M.¹ Li, S.H.² Gorls, H.³ Schollmeyer, D.⁴ Hillinger, M.⁵ Grabley, S.⁶ Sattler, I.⁷

10
- 78650186701
- Y. Igarashi, L. Yu, S. Miyanaga, T. Fukuda, N. Saitoh, H. Sakurai, I. Saiki, P. Alonso-Vega, M. E. Trujillo, J. Nat. Prod. 2010, 73, 1943-1946; for ent-Homoabyssomicins A and B, see
- (2010) J. Nat. Prod. , vol.73 , pp. 1943-1946
- Igarashi, Y.¹ Yu, L.² Miyanaga, S.³ Fukuda, T.⁴ Saitoh, N.⁵ Sakurai, H.⁶ Saiki, I.⁷ Alonso-Vega, P.⁸ Trujillo, M.E.⁹

11
- 79955643183
- M. A. Abdalla, P. P. Yadav, B. Dittrich, A. Schuffler, H. Laatsch, Org. Lett. 2011, 13, 2156-2159.
- (2011) Org. Lett. , vol.13 , pp. 2156-2159
- Abdalla, M.A.¹ Yadav, P.P.² Dittrich, B.³ Schuffler, A.⁴ Laatsch, H.⁵

12
- 0042261072
- Wiley-VCH, Veinheim
- For a book chapter on the abyssomicins, see:, K. C. Nicolaou, J. S. Chen, Classics in Total Synthesis III, Wiley-VCH, Veinheim, 2011.
- (2011) Classics in Total Synthesis III
- Nicolaou, K.C.¹ Chen, J.S.²

13
- 33646471049
- C. W. Zapf, B. A. Harrison, C. Drahl, E. J. Sorensen, Angew. Chem. 2005, 117, 6691-6695
- (2005) Angew. Chem. , vol.117 , pp. 6691-6695
- Zapf, C.W.¹ Harrison, B.A.² Drahl, C.³ Sorensen, E.J.⁴

14
- 27144521210
- Angew. Chem. Int. Ed. 2005, 44, 6533-6537.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 6533-6537

15
- 33748552666
- K. C. Nicolaou, S. T. Harrison, Angew. Chem. 2006, 118, 3334-3338
- (2006) Angew. Chem. , vol.118 , pp. 3334-3338
- Nicolaou, K.C.¹ Harrison, S.T.²

16
- 33746217394
- Angew. Chem. Int. Ed. 2006, 45, 3256-3260
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 3256-3260

17
- 33846195899
- K. C. Nicolaou, S. T. Harrison, J. Am. Chem. Soc. 2007, 129, 429-440
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 429-440
- Nicolaou, K.C.¹ Harrison, S.T.²

18
- 63849306648
- K. C. Nicolaou, S. T. Harrison, J. S. Chen, Synthesis 2009, 33-42.
- (2009) Synthesis , pp. 33-42
- Nicolaou, K.C.¹ Harrison, S.T.² Chen, J.S.³

19
- 33646471096
- E. A. Couladouros, E. A. Bouzas, A. D. Magos, Tetrahedron 2006, 62, 5272-5279.
- (2006) Tetrahedron , vol.62 , pp. 5272-5279
- Couladouros, E.A.¹ Bouzas, E.A.² Magos, A.D.³

20
- 27644479911
- B. B. Snider, Y. Zhou, Org. Lett. 2005, 7, 4939-4941
- (2005) Org. Lett. , vol.7 , pp. 4939-4941
- Snider, B.B.¹ Zhou, Y.²

21
- 13844269068
- J.-P. Rath, M. Eipert, S. Kinast, M. E. Maier, Synlett 2005, 314-318
- (2005) Synlett , pp. 314-318
- Rath, J.-P.¹ Eipert, M.² Kinast, S.³ Maier, M.E.⁴

22
- 22244465885
- J.-P. Rath, S. Kinast, M. E. Maier, Org. Lett. 2005, 7, 3089-3092
- (2005) Org. Lett. , vol.7 , pp. 3089-3092
- Rath, J.-P.¹ Kinast, S.² Maier, M.E.³

23
- 26444585921
- A. L. Zografos, A. Yiotakis, D. Georgiadis, Org. Lett. 2005, 7, 4515-4518
- (2005) Org. Lett. , vol.7 , pp. 4515-4518
- Zografos, A.L.¹ Yiotakis, A.² Georgiadis, D.³

24
- 84861610282
- Ph.D. Dissertation, University of Tübingen
- S. Kinast, Strategien zur Synthese von Abyssomicin C Derivaten. Ph.D. Dissertation, University of Tübingen, 2008.
- (2008) Strategien Zur Synthese von Abyssomicin C Derivaten
- Kinast, S.¹

25
- 0035932568
- M. T. Crimmins, J. D. Katz, L. C. McAtee, E. A. Tabet, S. J. Kirincich, Org. Lett. 2001, 3, 949-952. Note that within the paper that is referenced above, the oxazolidinone in structures 10 and 11 (Scheme 2) is drawn with the R configuration; this is an error, the correct configuration is S, and the aldol reaction follows the normal stereochemical course, as expected for Evans oxazolidinones (from a personal communication with Prof. M. T. Crimmins).
- (2001) Org. Lett. , vol.3 , pp. 949-952
- Crimmins, M.T.¹ Katz, J.D.² McAtee, L.C.³ Tabet, E.A.⁴ Kirincich, S.J.⁵

26
- 17744400729
- A. Minatti, K. H. Dotz, J. Org. Chem. 2005, 70, 3745-3748.
- (2005) J. Org. Chem. , vol.70 , pp. 3745-3748
- Minatti, A.¹ Dotz, K.H.²

27
- 0000776391
- E. J. Corey, H. Cho, C. Rucker, D. H. Hua, Tetrahedron Lett. 1981, 22, 3455-3458.
- (1981) Tetrahedron Lett. , vol.22 , pp. 3455-3458
- Corey, E.J.¹ Cho, H.² Rucker, C.³ Hua, D.H.⁴

28
- 0001118624
- A. G. M. Barrett, D. Hamprecht, M. Ohkubo, J. Org. Chem. 1997, 62, 9376-9378.
- (1997) J. Org. Chem. , vol.62 , pp. 9376-9378
- Barrett, A.G.M.¹ Hamprecht, D.² Ohkubo, M.³

29
- 0345825852
- N. Vignola, B. List, J. Am. Chem. Soc. 2004, 126, 450-451.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 450-451
- Vignola, N.¹ List, B.²

30
- 36849014339
- additions and corrections
- F. Bihelovic, R. Matovic, B. Vulovic, R. N. Saicic, Org. Lett. 2007, 9, 5063-5066; additions and corrections
- (2007) Org. Lett. , vol.9 , pp. 5063-5066
- Bihelovic, F.¹ Matovic, R.² Vulovic, B.³ Saicic, R.N.⁴

31
- 38349185623
- F. Bihelovic, R. Matovic, B. Vulovic, R. N. Saicic, Org. Lett. 2007, 9, 5649
- (2007) Org. Lett. , vol.9 , pp. 5649
- Bihelovic, F.¹ Matovic, R.² Vulovic, B.³ Saicic, R.N.⁴

32
- 70449356896
- corrigendum
- B. Vulovic, F. Bihelovic, R. Matovic, R. N. Saicic, Tetrahedron 2009, 65, 10485-10494; corrigendum
- (2009) Tetrahedron , vol.65 , pp. 10485-10494
- Vulovic, B.¹ Bihelovic, F.² Matovic, R.³ Saicic, R.N.⁴

33
- 77950050154
- B. Vulovic, F. Bihelovic, R. Matovic, R. N. Saicic, Tetrahedron 2010, 66, 3275.
- (2010) Tetrahedron , vol.66 , pp. 3275
- Vulovic, B.¹ Bihelovic, F.² Matovic, R.³ Saicic, R.N.⁴

34
- 70349943846
- Z. Zhao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745-2755
- (2009) Chem. Soc. Rev. , vol.38 , pp. 2745-2755
- Zhao, Z.¹ Zhang, H.²

35
- 77952637874
- C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999-3025.
- (2010) Eur. J. Org. Chem. , pp. 2999-3025
- Zhong, C.¹ Shi, X.²

36
- 0038203414
- B. G. Jellerichs, J.-R. Kong, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 7758-7759; for the first example of a combination of enamine catalysis and organotransition metal catalysis, see
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 7758-7759
- Jellerichs, B.G.¹ Kong, J.-R.² Krische, M.J.³

37
- 33750613873
- I. Ibrahem, A. Cordova, Angew. Chem. 2006, 118, 1986-1990
- (2006) Angew. Chem. , vol.118 , pp. 1986-1990
- Ibrahem, I.¹ Cordova, A.²

38
- 33646573235
- Angew. Chem. Int. Ed. 2006, 45, 1952-1956.
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1952-1956

39
- 34248637761
- A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105
- (2006) Angew. Chem. , vol.118 , pp. 8064-8105
- Hashmi, A.S.K.¹ Hutchings, G.J.²

40
- 33845546747
- Angew. Chem. Int. Ed. 2006, 45, 7896-7936
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7896-7936

41
- 33845247117
- L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271-2296
- (2006) Adv. Synth. Catal. , vol.348 , pp. 2271-2296
- Zhang, L.¹ Sun, J.² Kozmin, S.A.³

42
- 33947578482
- D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403
- (2007) Nature , vol.446 , pp. 395-403
- Gorin, D.J.¹ Toste, F.D.²

43
- 84855281169
- A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519
- (2007) Angew. Chem. , vol.119 , pp. 3478-3519
- Fürstner, A.¹ Davies, P.W.²

44
- 34250824768
- Angew. Chem. Int. Ed. 2007, 46, 3410-3449
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3410-3449

45
- 34547510627
- A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
- (2007) Chem. Rev. , vol.107 , pp. 3180-3211
- Hashmi, A.S.K.¹

46
- 33846207883
- E. Jiménez-Núñez, A. Echavarren, Chem. Commun. 2007, 333-346
- (2007) Chem. Commun. , pp. 333-346
- Jiménez-Núñez, E.¹ Echavarren, A.²

47
- 51049121927
- Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265
- (2008) Chem. Rev. , vol.108 , pp. 3239-3265
- Li, Z.¹ Brouwer, C.² He, C.³

48
- 51249100498
- A. Arcadi, Chem. Rev. 2008, 108, 3266-3325
- (2008) Chem. Rev. , vol.108 , pp. 3266-3325
- Arcadi, A.¹

49
- 51049105959
- D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378
- (2008) Chem. Rev. , vol.108 , pp. 3351-3378
- Gorin, D.J.¹ Sherry, B.D.² Toste, F.D.³

50
- 51049114031
- N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395-3442
- (2008) Chem. Rev. , vol.108 , pp. 3395-3442
- Patil, N.T.¹ Yamamoto, Y.²

51
- 50949125916
- A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766-1775
- (2008) Chem. Soc. Rev. , vol.37 , pp. 1766-1775
- Hashmi, A.S.K.¹ Rudolph, M.²

52
- 50949117366
- N. Marion, S. P. Nolan, Chem. Soc. Rev. 2008, 37, 1776-1782
- (2008) Chem. Soc. Rev. , vol.37 , pp. 1776-1782
- Marion, N.¹ Nolan, S.P.²

53
- 84857594600
- M. Rudolph, S. Hashmi, Chem. Soc. Rev. 2012, 41, 2448-2462.
- (2012) Chem. Soc. Rev. , vol.41 , pp. 2448-2462
- Rudolph, M.¹ Hashmi, S.²

54
- 25444522675
- N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133-4136.
- (2005) Org. Lett. , vol.7 , pp. 4133-4136
- Mézailles, N.¹ Ricard, L.² Gagosz, F.³

55
- 33748457297
- For an improved procedure for the preparation of cis-2,4- dimethylglutaranhydride, see:, R. N. Saicic, Synth. Commun. 2006, 36, 2559-2562.
- (2006) Synth. Commun. , vol.36 , pp. 2559-2562
- Saicic, R.N.¹

56
- 0141452587
- U. C. Dyer, J. A. Robinson, J. Chem. Soc. Perkin Trans. 1 1988, 53-60
- (1988) J. Chem. Soc. Perkin Trans. 1 , pp. 53-60
- Dyer, U.C.¹ Robinson, J.A.²

57
- 0036959703
- R. W. Hoffmann, U. Schopfer, G. Müller, T. Brand, Helv. Chim. Acta 2002, 85, 4424-4441.
- (2002) Helv. Chim. Acta , vol.85 , pp. 4424-4441
- Hoffmann, R.W.¹ Schopfer, U.² Müller, G.³ Brand, T.⁴

58
- 33845373603
- K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408-7410.
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 7408-7410
- Takai, K.¹ Nitta, K.² Utimoto, K.³

59
- 0000316683
- K. Takai, K. Kimura, T. Kuroda, T. Hiyama, H. Nozaki, Tetrahedron Lett. 1983, 24, 5281-5284
- (1983) Tetrahedron Lett. , vol.24 , pp. 5281-5284
- Takai, K.¹ Kimura, K.² Kuroda, T.³ Hiyama, T.⁴ Nozaki, H.⁵

60
- 33845375686
- H. Jin, J. Uenishi, W. J. Christ, Y. Kishi, J. Am. Chem. Soc. 1986, 108, 5644-5646.
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 5644-5646
- Jin, H.¹ Uenishi, J.² Christ, W.J.³ Kishi, Y.⁴

61
- 3042741556
- D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7278.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 7277-7278
- Dess, D.B.¹ Martin, J.C.²

62
- 84861621062
- 2, 120 °C
- 2, 120 °C.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.