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Volumn 11, Issue 13, 2013, Pages 2116-2139

Modular synthesis of polyene side chain analogues of the potent macrolide antibiotic etnangien by a flexible coupling strategy based on hetero-bis-metallated alkenes

(5) Altendorfer, Mario a Raja, Aruna b Sasse, Florenz b Irschik, Herbert b Menche, Dirk a,c

a UNIVERSITY OF HEIDELBERG (Germany)

b HELMHOLTZ CENTRE FOR INFECTION RESEARCH (Germany)

c UNIVERSITY OF BONN (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-PROLIFERATIVE ACTIVITIES; BI-FUNCTIONAL; BUILDING BLOCKES; CONCISE SYNTHESIS; MACROLIDE ANTIBIOTICS; MODULAR SYNTHESIS; RNA POLYMERASE; SIDE-CHAIN ANALOGUES;

FLEXIBLE COUPLINGS; RNA;

HYDROCARBONS;

ALKENE; ANTIINFECTIVE AGENT; DNA DIRECTED RNA POLYMERASE; ENZYME INHIBITOR; ETNANGIEN; MACROLIDE; ORGANOMETALLIC COMPOUND; POLYENE;

ANIMAL; ARTICLE; BACILLUS SUBTILIS; CELL CULTURE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CORYNEBACTERIUM; DOSE RESPONSE; DRUG ANTAGONISM; DRUG EFFECT; FIBROBLAST; METABOLISM; MICROBIAL SENSITIVITY TEST; MOUSE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKENES; ANIMALS; ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; CELL PROLIFERATION; CELLS, CULTURED; CORYNEBACTERIUM; DNA-DIRECTED RNA POLYMERASES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; FIBROBLASTS; MACROLIDES; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; POLYENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84874822098 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c2ob26906f Document Type: Article

Times cited : (28)

References (55)

1
- 80051751439
- S. J. Lee T. M. Anderson M. D. Burke Angew. Chem., Int. Ed. 2010 122 9044
- (2010) Angew. Chem., Int. Ed. , vol.122 , pp. 9044
- Lee, S.J.¹ Anderson, T.M.² Burke, M.D.³

2
- 0030111156
- G. M. Strunz H. J. Finlay Can. J. Chem. 1996 74 419
- (1996) Can. J. Chem. , vol.74 , pp. 419
- Strunz, G.M.¹ Finlay, H.J.²

3
- 80052815516
- T. Brautaset H. Sletta K. F. Degnes O. N. Sekurova I. Bakke O. Volokhan T. Andreassen T. E. Ellingsen S. B. Zotchev Appl. Environ. Microbiol. 2011 77 6636
- (2011) Appl. Environ. Microbiol. , vol.77 , pp. 6636
- Brautaset, T.¹ Sletta, H.² Degnes, K.F.³ Sekurova, O.N.⁴ Bakke, I.⁵ Volokhan, O.⁶ Andreassen, T.⁷ Ellingsen, T.E.⁸ Zotchev, S.B.⁹

4
- 54849419509
- D. Menche F. Arikan O. Perlova N. Horstmann W. Ahlbrecht S. C. Wenzel R. Jansen H. Irschik R. Müller J. Am. Chem. Soc. 2008 130 14234
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14234
- Menche, D.¹ Arikan, F.² Perlova, O.³ Horstmann, N.⁴ Ahlbrecht, W.⁵ Wenzel, S.C.⁶ Jansen, R.⁷ Irschik, H.⁸ Müller, R.⁹

5
- 84874919972
- DE 195 30 980 A1: 1-7 (5.2.1998) For reviews on polyketides from myxobacteria, see
- G. Höfle, H. Reichenbach, H. Irschik and D. Schummer, German Pat., DE 195 30 980 A1: 1-7 (5.2.1998)
- German Pat.
- Höfle, G.¹ Reichenbach, H.² Irschik, H.³ Schummer, D.⁴

6
- 52649154523
- D. Menche Nat. Prod. Rep. 2008 25 905
- (2008) Nat. Prod. Rep. , vol.25 , pp. 905
- Menche, D.¹

7
- 77955670903
- K. J. Weissman R. Müller Nat. Prod. Rep. 2010 27 1276
- (2010) Nat. Prod. Rep. , vol.27 , pp. 1276
- Weissman, K.J.¹ Müller, R.²

8
- 69049087735
- P. Li J. Li F. Arikan W. Ahlbrecht M. Dieckmann D. Menche J. Am. Chem. Soc. 2009 131 11678
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 11678
- Li, P.¹ Li, J.² Arikan, F.³ Ahlbrecht, W.⁴ Dieckmann, M.⁵ Menche, D.⁶

9
- 77950989172
- P. Li J. Li F. Arikan W. Ahlbrecht M. Dieckmann D. Menche J. Org. Chem. 2010 75 2429
- (2010) J. Org. Chem. , vol.75 , pp. 2429
- Li, P.¹ Li, J.² Arikan, F.³ Ahlbrecht, W.⁴ Dieckmann, M.⁵ Menche, D.⁶

10
- 74049122041
- D. Menche P. Li H. Irschik Bioorg. Med. Chem. Lett. 2010 20 939
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 939
- Menche, D.¹ Li, P.² Irschik, H.³

11
- 34447344496
- H. Irschik D. Schummer G. Höfle H. Reichenbach H. Steinmetz R. Jansen J. Nat. Prod. 2007 70 1060
- (2007) J. Nat. Prod. , vol.70 , pp. 1060
- Irschik, H.¹ Schummer, D.² Höfle, G.³ Reichenbach, H.⁴ Steinmetz, H.⁵ Jansen, R.⁶

12
- 1842713108
- S. Darst Trends Biochem. Sci. 2004 29 159
- (2004) Trends Biochem. Sci. , vol.29 , pp. 159
- Darst, S.¹

13
- 34547638220
- I. Chopra Curr. Opin. Invest. Drugs 2007 8 600
- (2007) Curr. Opin. Invest. Drugs , vol.8 , pp. 600
- Chopra, I.¹

14
- 84859252060
- D. Haebich F. von Nussbaum Angew. Chem. 2009 121 3447
- (2009) Angew. Chem. , vol.121 , pp. 3447
- Haebich, D.¹ Von Nussbaum, F.²

15
- 20444484806
- R. S. Coleman M. C. Walczak Org. Lett. 2005 7 2289
- (2005) Org. Lett. , vol.7 , pp. 2289
- Coleman, R.S.¹ Walczak, M.C.²

16
- 28044453913
- R. S. Coleman M. C. Walczak E. L. Campbell J. Am. Chem. Soc. 2005 127 16038
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 16038
- Coleman, R.S.¹ Walczak, M.C.² Campbell, E.L.³

17
- 33845939119
- R. S. Coleman M. C. Walczak J. Org. Chem. 2006 71 9841
- (2006) J. Org. Chem. , vol.71 , pp. 9841
- Coleman, R.S.¹ Walczak, M.C.²

18
- 33645454831
- R. S. Coleman X. Lu Chem. Commun. 2006 423
- (2006) Chem. Commun. , pp. 423
- Coleman, R.S.¹ Lu, X.²

19
- 34247101151
- R. S. Coleman X. Lu I. Modolo J. Am. Chem. Soc. 2007 129 3826
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 3826
- Coleman, R.S.¹ Lu, X.² Modolo, I.³

20
- 0003115131
- Part of these results have been reported in preliminary form
- F. Lhermitte B. Carboni Synlett 1996 377
- (1996) Synlett , pp. 377
- Lhermitte, F.¹ Carboni, B.²

21
- 84865146727
- M. Altendorfer H. Irschik D. Menche Bioorg. Med. Chem. Lett. 2012 22 5731
- (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 5731
- Altendorfer, M.¹ Irschik, H.² Menche, D.³

22
- 84864248645
- For construction of polyene systems via iterative cross coupling see
- M. Altendorfer D. Menche Chem. Commun. 2012 48 8267
- (2012) Chem. Commun. , vol.48 , pp. 8267
- Altendorfer, M.¹ Menche, D.²

23
- 34249828956
- E. P. Gillis M. D. Burke J. Am. Chem. Soc. 2007 129 6716
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 6716
- Gillis, E.P.¹ Burke, M.D.²

24
- 54849403713
- E. P. Gillis M. D. Burke J. Am. Chem. Soc. 2008 130 14084
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14084
- Gillis, E.P.¹ Burke, M.D.²

25
- 62049085616
- B. E. Uno E. P. Gillis M. D. Burke Tetrahedron 2009 65 3130
- (2009) Tetrahedron , vol.65 , pp. 3130
- Uno, B.E.¹ Gillis, E.P.² Burke, M.D.³

26
- 70349897220
- C. Wang F. Glorius Angew. Chem., Int. Ed. 2009 48 5240
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5240
- Wang, C.¹ Glorius, F.²

27
- 78449258277
- 3a-c are commercially available; for preparation of alkynoles 3d and 3e, see
- S. J. Lee T. M. Anderson M. D. Burke Angew. Chem., Int. Ed. 2010 49 8860
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 8860
- Lee, S.J.¹ Anderson, T.M.² Burke, M.D.³

28
- 77951777397
- B. Sui E. A.-H. Yeh D. P. Curran J. Org. Chem. 2010 75 2942
- (2010) J. Org. Chem. , vol.75 , pp. 2942
- Sui, B.¹ Yeh, E.A.-H.² Curran, D.P.³

29
- 51049124099
- A. Darwish A. Lang T. Kim J. M. Chong Org. Lett. 2008 10 861
- (2008) Org. Lett. , vol.10 , pp. 861
- Darwish, A.¹ Lang, A.² Kim, T.³ Chong, J.M.⁴

30
- 0027997412
- S. V. Ley J. Norman W. P. Griffith S. P. Mardsen Synthesis 1994 7 639
- (1994) Synthesis , vol.7 , pp. 639
- Ley, S.V.¹ Norman, J.² Griffith, W.P.³ Mardsen, S.P.⁴

31
- 0031025353
- I. Paterson C. Watson K.-S. Yeung P. A. Wallace R. A. Ward J. Org. Chem. 1997 62 452
- (1997) J. Org. Chem. , vol.62 , pp. 452
- Paterson, I.¹ Watson, C.² Yeung, K.-S.³ Wallace, P.A.⁴ Ward, R.A.⁵

32
- 0001782661
- K. Takai N. Shinomiya H. Kaihara N. Yoshida T. Moriwake Synlett 1995 963
- (1995) Synlett , pp. 963
- Takai, K.¹ Shinomiya, N.² Kaihara, H.³ Yoshida, N.⁴ Moriwake, T.⁵

33
- 0141521559
- No induction was obtained using the Carreira procedure
- J. A. Marshall M. P. Bourbeu Org. Lett. 2003 5 3197
- (2003) Org. Lett. , vol.5 , pp. 3197
- Marshall, J.A.¹ Bourbeu, M.P.²

34
- 0041407526
- D. E. Frantz R. Fässler E. M. Carreira J. Am. Chem. Soc. 2000 122 1806
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 1806
- Frantz, D.E.¹ Fässler, R.² Carreira, E.M.³

35
- 33847801219
- D. W. Hart T. F. Blackburn J. Schwartz J. Am. Chem. Soc. 1975 97 679
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 679
- Hart, D.W.¹ Blackburn, T.F.² Schwartz, J.³

36
- 0030607168
- P. Wipf H. Jahn Tetrahedron 1996 52 12853
- (1996) Tetrahedron , vol.52 , pp. 12853
- Wipf, P.¹ Jahn, H.²

37
- 33748617140
- Z. Huang E. Negishi Org. Lett. 2006 8 3675
- (2006) Org. Lett. , vol.8 , pp. 3675
- Huang, Z.¹ Negishi, E.²

38
- 13444249837
- D. Strand T. Rein Org. Lett. 2005 7 199
- (2005) Org. Lett. , vol.7 , pp. 199
- Strand, D.¹ Rein, T.²

39
- 77957311255
- T. Brodmann D. Jansen M. Kalesse J. Am. Chem. Soc. 2010 132 13610
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 13610
- Brodmann, T.¹ Jansen, D.² Kalesse, M.³

40
- 0040746033
- H. X. Zhang F. Guibe G. Balavoine J. Org. Chem. 1990 55 1857
- (1990) J. Org. Chem. , vol.55 , pp. 1857
- Zhang, H.X.¹ Guibe, F.² Balavoine, G.³

41
- 43849098048
- K. Takao N. Hayakawa R. Yamada T. Yamaguchi U. Morita S. Kawasaki K. Tadano Angew. Chem., Int. Ed. 2008 47 3426
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3426
- Takao, K.¹ Hayakawa, N.² Yamada, R.³ Yamaguchi, T.⁴ Morita, U.⁵ Kawasaki, S.⁶ Tadano, K.⁷

42
- 0023865490
- P. M. Gannett D. L. Nagel P. J. Reilly T. Lawson J. Shape B. Toth J. Org. Chem. 1988 53 1064
- (1988) J. Org. Chem. , vol.53 , pp. 1064
- Gannett, P.M.¹ Nagel, D.L.² Reilly, P.J.³ Lawson, T.⁴ Shape, J.⁵ Toth, B.⁶

43
- 33845375446
- H. C. Brown K. S. Bhat J. Am. Chem. Soc. 1986 108 5919
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 5919
- Brown, H.C.¹ Bhat, K.S.²

44
- 33845374534
- P. K. Jadhav K. S. Bhat P. T. Perumal H. C. Brown J. Org. Chem. 1986 51 432
- (1986) J. Org. Chem. , vol.51 , pp. 432
- Jadhav, P.K.¹ Bhat, K.S.² Perumal, P.T.³ Brown, H.C.⁴

45
- 0001646391
- U. S. Racherla H. C. Brown J. Org. Chem. 1991 56 401
- (1991) J. Org. Chem. , vol.56 , pp. 401
- Racherla, U.S.¹ Brown, H.C.²

46
- 84865144294
- The ee and the configuration of the new stereogenic center were determined using Mosher's ester analysis. See Experimental part for full details
- U. S. Racherla Y. Liao H. C. Brown J. Org. Chem. 1992 57 8614
- (1992) J. Org. Chem. , vol.57 , pp. 8614
- Racherla, U.S.¹ Liao, Y.² Brown, H.C.³

47
- 33845373603
- K. Takai K. Nitta K. Utimoto J. Am. Chem. Soc. 1986 108 7408
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 7408
- Takai, K.¹ Nitta, K.² Utimoto, K.³

48
- 0000000692
- T. Okazoe K. Takai K. Utimoto J. Am. Chem. Soc. 1987 109 951
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 951
- Okazoe, T.¹ Takai, K.² Utimoto, K.³

49
- 2642676149
- D. A. Evans W. C. Black J. Am. Chem. Soc. 1993 115 4497
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4497
- Evans, D.A.¹ Black, W.C.²

50
- 33845281119
- J. K. Stille B. L. Groh J. Am. Chem. Soc. 1987 109 813
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 813
- Stille, J.K.¹ Groh, B.L.²

51
- 2042507954
- N. Miyaura A. Suzuki Chem. Rev. 1995 95 2457
- (1995) Chem. Rev. , vol.95 , pp. 2457
- Miyaura, N.¹ Suzuki, A.²

52
- 0346786657
- A. Suzuki J. Organomet. Chem. 1999 576 147
- (1999) J. Organomet. Chem. , vol.576 , pp. 147
- Suzuki, A.¹

53
- 30944464654
- A. Gopalarathnam S. Nelson Org. Lett. 2006 8 7
- (2006) Org. Lett. , vol.8 , pp. 7
- Gopalarathnam, A.¹ Nelson, S.²

54
- 33847770029
- Y. Kaburagi Y. Kishi Org. Lett. 2007 9 723
- (2007) Org. Lett. , vol.9 , pp. 723
- Kaburagi, Y.¹ Kishi, Y.²

55
- 0942277395
- J. M. Seco E. Quinoa R. Riguera Chem. Rev. 2004 104 17
- (2004) Chem. Rev. , vol.104 , pp. 17
- Seco, J.M.¹ Quinoa, E.² Riguera, R.³

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