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Angewandte Chemie - International Edition

Volumn 51, Issue 30, 2012, Pages 7507-7510

Sequential C sp3-H arylation and olefination: Total synthesis of the proposed structure of pipercyclobutanamide a

(3) Gutekunst, Will R a Gianatassio, Ryan a Baran, Phil S a

a SCRIPPS RESEARCH INSTITUTE (United States)

Author keywords

C H functionalization; natural products; palladium; small rings; synthesis design

Indexed keywords

ARYLATIONS; C-C BONDS; C-H FUNCTIONALIZATION; CYCLOBUTANES; FUNCTIONALIZATIONS; NATURAL PRODUCTS; OLEFINATION; SMALL RINGS; SYNTHESIS DESIGN; TOTAL SYNTHESIS;

BUTANE; PALLADIUM;

CHEMICAL REACTIONS;

ALKENE; AMIDE; BIOLOGICAL PRODUCT; CYCLOBUTANE DERIVATIVE; PALLADIUM;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKENES; AMIDES; BIOLOGICAL AGENTS; CYCLOBUTANES; PALLADIUM; PIPER;

EID: 84864191250 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201203897 Document Type: Article

Times cited : (207)

References (42)

1
- 81855199815
- for reviews on C-H functionalization in synthesis
- W. R. Gutekunst, P. S. Baran, J. Am. Chem. Soc. 2011, 133, 19076-19079; for reviews on C-H functionalization in synthesis
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 19076-19079
- Gutekunst, W.R.¹ Baran, P.S.²

2
- 0031831331
- D. F. Taber, S. E. Stiriba, Chem. Eur. J. 1998, 4, 990-992
- (1998) Chem. Eur. J. , vol.4 , pp. 990-992
- Taber, D.F.¹ Stiriba, S.E.²

3
- 33645674829
- K. Godula, D. Sames, Science 2006, 312, 67-72
- (2006) Science , vol.312 , pp. 67-72
- Godula, K.¹ Sames, D.²

4
- 38749146550
- H. M. Davies, J. R. Manning, Nature 2008, 451, 417-424
- (2008) Nature , vol.451 , pp. 417-424
- Davies, H.M.¹ Manning, J.R.²

5
- 77954842094
- Y. Ishihara, P. S. Baran, Synlett 2010, 1733-1745
- (2010) Synlett , pp. 1733-1745
- Ishihara, Y.¹ Baran, P.S.²

6
- 79958774552
- W. R. Gutekunst, P. S. Baran, Chem. Soc. Rev. 2011, 40, 1976-1991
- (2011) Chem. Soc. Rev. , vol.40 , pp. 1976-1991
- Gutekunst, W.R.¹ Baran, P.S.²

7
- 79958848824
- L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011, 40, 1885-1898
- (2011) Chem. Soc. Rev. , vol.40 , pp. 1885-1898
- McMurray, L.¹ O'Hara, F.² Gaunt, M.J.³

8
- 84889086895
- DOI
- T. Brückl, R. D. Baxter, Y. Ishihara, P. S. Baran, Acc. Chem. Res. 2011, DOI:.
- (2011) Acc. Chem. Res.
- Brückl, T.¹

9
- 1842662350
- F.-P. Lee, Y.-C. Chen, J.-J. Chen, I.-L. Tsai, I.-S. Chen, Helv. Chim. Acta 2004, 87, 463-468
- (2004) Helv. Chim. Acta , vol.87 , pp. 463-468
- Lee, F.-P.¹ Chen, Y.-C.² Chen, J.-J.³ Tsai, I.-L.⁴ Chen, I.-S.⁵

10
- 21344469115
- I.-L. Tsai, F.-P. Lee, C.-C. Wu, C.-Y. Duh, T. Ishikawa, J.-J. Chen, Y.-C. Chen, H. Seki, I.-S. Chen, Planta Med. 2005, 71, 535-542.
- (2005) Planta Med. , vol.71 , pp. 535-542
- Tsai, I.-L.¹ Lee, F.-P.² Wu, C.-C.³ Duh, C.-Y.⁴ Ishikawa, T.⁵ Chen, J.-J.⁶ Chen, Y.-C.⁷ Seki, H.⁸ Chen, I.-S.⁹

11
- 0035952967
- Y. Fujiwara, K. Naithou, T. Miyazaki, K. Hashimoto, K. Mori, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 2497-2499
- (2001) Tetrahedron Lett. , vol.42 , pp. 2497-2499
- Fujiwara, Y.¹ Naithou, K.² Miyazaki, T.³ Hashimoto, K.⁴ Mori, K.⁵ Yamamoto, Y.⁶

12
- 13844318476
- K. Wei, W. Li, K. Koike, Y. Chen, T. Nikaido, J. Org. Chem. 2005, 70, 1164-1176
- (2005) J. Org. Chem. , vol.70 , pp. 1164-1176
- Wei, K.¹ Li, W.² Koike, K.³ Chen, Y.⁴ Nikaido, T.⁵

13
- 0036311050
- S. Tsukamoto, K. Tomise, K. Miyakawa, B. C. Cha, T. Abe, T. Hamada, H. Hirota, T. Ohta, Bioorg. Med. Chem. 2002, 10, 2981-2985
- (2002) Bioorg. Med. Chem. , vol.10 , pp. 2981-2985
- Tsukamoto, S.¹ Tomise, K.² Miyakawa, K.³ Cha, B.C.⁴ Abe, T.⁵ Hamada, T.⁶ Hirota, H.⁷ Ohta, T.⁸

14
- 33744913556
- Subehan, T. Usia, S. Kadota, Y. Tezuka, Planta Med. 2006, 72, 527-532
- (2006) Planta Med. , vol.72 , pp. 527-532
- Subehan¹ Usia, T.² Kadota, S.³ Tezuka, Y.⁴

15
- 0033031671
- R. L. Sharma, M. Kumari, N. Kumar, A. Prabhakar, Fitoterapia 1999, 70, 144-147
- (1999) Fitoterapia , vol.70 , pp. 144-147
- Sharma, R.L.¹ Kumari, M.² Kumar, N.³ Prabhakar, A.⁴

16
- 71749121016
- H. Matsuda, K. Ninomiya, T. Morikawa, D. Yasuda, I. Yamaguchi, M. Yoshikawa, Bioorg. Med. Chem. 2009, 17, 7313-7323.
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 7313-7323
- Matsuda, H.¹ Ninomiya, K.² Morikawa, T.³ Yasuda, D.⁴ Yamaguchi, I.⁵ Yoshikawa, M.⁶

17
- 0002591690
- I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119-1122
- (1967) Tetrahedron Lett. , vol.8 , pp. 1119-1122
- Moritani, I.¹ Fujiwara, Y.²

18
- 0034867872
- C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639.
- (2001) Acc. Chem. Res. , vol.34 , pp. 633-639
- Jia, C.¹ Kitamura, T.² Fujiwara, Y.³

19
- 77949801096
- M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680-3681
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 3680-3681
- Wasa, M.¹ Engle, K.M.² Yu, J.-Q.³

20
- 83055161417
- M. Wasa, K. M. Engle, D. W. Lin, E. J. Yoo, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 19598-19601
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 19598-19601
- Wasa, M.¹ Engle, K.M.² Lin, D.W.³ Yoo, E.J.⁴ Yu, J.-Q.⁵

21
- 79955403712
- K. J. Stowers, K. C. Fortner, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 6541-6544
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 6541-6544
- Stowers, K.J.¹ Fortner, K.C.² Sanford, M.S.³

22
- 84858032510
- G. He, G. Chen, Angew. Chem. 2011, 123, 5298-5302
- (2011) Angew. Chem. , vol.123 , pp. 5298-5302
- He, G.¹ Chen, G.²

23
- 79956061678
- Angew. Chem. Int. Ed. 2011, 50, 5192-5196
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5192-5196

24
- 0037048663
- B. D. Dangel, K. Godula, S. W. Youn, B. Sezen, D. Sames, J. Am. Chem. Soc. 2002, 124, 11856-11857.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 11856-11857
- Dangel, B.D.¹ Godula, K.² Youn, S.W.³ Sezen, B.⁴ Sames, D.⁵

25
- 77949784030
- D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965-3972.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 3965-3972
- Shabashov, D.¹ Daugulis, O.²

26
- 84855680087
- F. Frébault, M. Luparia, M. T. Oliveira, R. Goddard, N. Maulide, Angew. Chem. 2010, 122, 5807-5811
- (2010) Angew. Chem. , vol.122 , pp. 5807-5811
- Frébault, F.¹ Luparia, M.² Oliveira, M.T.³ Goddard, R.⁴ Maulide, N.⁵

27
- 77955341231
- Angew. Chem. Int. Ed. 2010, 49, 5672-5676
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 5672-5676

28
- 0001488571
- E. J. Corey, J. Streith, J. Am. Chem. Soc. 1964, 86, 950-951
- (1964) J. Am. Chem. Soc. , vol.86 , pp. 950-951
- Corey, E.J.¹ Streith, J.²

29
- 0038132777
- H. Javaheripour, D. C. Neckers, J. Org. Chem. 1977, 42, 1844-1850
- (1977) J. Org. Chem. , vol.42 , pp. 1844-1850
- Javaheripour, H.¹ Neckers, D.C.²

30
- 84863822399
- M. Luparia, M. T. Oliveira, D. Audisio, F. Frébault, R. Goddard, N. Maulide, Angew. Chem. 2011, 123, 12840-12844
- (2011) Angew. Chem. , vol.123 , pp. 12840-12844
- Luparia, M.¹ Oliveira, M.T.² Audisio, D.³ Frébault, F.⁴ Goddard, R.⁵ Maulide, N.⁶

31
- 84255198616
- Angew. Chem. Int. Ed. 2011, 50, 12631-12635.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 12631-12635

32
- 25444458063
- V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154-13155
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 13154-13155
- Zaitsev, V.G.¹ Shabashov, D.² Daugulis, O.³

33
- 0041734018
- This strategy was inspired by Barton's clever use of enolate anions as protecting groups
- This strategy was inspired by Barton's clever use of enolate anions as protecting groups:, D. H. R. Barton, R. H. Hesse, C. Wilshire, M. M. Pechet, J. Chem. Soc. Perkin Trans. 1 1977, 1075-1079.
- (1977) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 1075-1079
- Barton, D.H.R.¹ Hesse, R.H.² Wilshire, C.³ Pechet, M.M.⁴

34
- 84864237328
- (Genelabs Technologies, Inc.), WO 2009023179, other methods for the direct reduction of secondary amides to aldehydes
- F. U. Schmitz, V. W.-F. Tai, R. Rai, C. D. Roberts, A. D. M. Abadi, S. Baskaran, I. Slobodov, J. Maung, M. L. Neitzel, (Genelabs Technologies, Inc.), WO 2009023179, 2009; other methods for the direct reduction of secondary amides to aldehydes
- (2009)
- Schmitz, F.U.¹ Tai, V.W.-F.² Rai, R.³ Roberts, C.D.⁴ Abadi, A.D.M.⁵ Baskaran, S.⁶ Slobodov, I.⁷ Maung, J.⁸ Neitzel, M.L.⁹

35
- 77956640932
- G. Pelletier, W. S. Bechara, A. B. Charette, J. Am. Chem. Soc. 2010, 132, 12817-12819
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 12817-12819
- Pelletier, G.¹ Bechara, W.S.² Charette, A.B.³

36
- 0006707299
- S. Bower, K. A. Kreutzer, S. L. Buchwald, Angew. Chem. 1996, 108, 1662-1664
- (1996) Angew. Chem. , vol.108 , pp. 1662-1664
- Bower, S.¹ Kreutzer, K.A.² Buchwald, S.L.³

37
- 0029738189
- Angew. Chem. Int. Ed. Engl. 1996, 35, 1515-1516
- (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1515-1516

38
- 33947409881
- J. T. Spletstoser, J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc. 2007, 129, 3408-3419.
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 3408-3419
- Spletstoser, J.T.¹ White, J.M.² Tunoori, A.R.³ Georg, G.I.⁴

39
- 68749089734
- K. Ando, S. Nagaya, Y. Tarumi, Tetrahedron Lett. 2009, 50, 5689-5691.
- (2009) Tetrahedron Lett. , vol.50 , pp. 5689-5691
- Ando, K.¹ Nagaya, S.² Tarumi, Y.³

40
- 84864221112
- DOI:; Angew. Chem. Int. Ed. 2012, DOI
- While this work was in progress, we became aware of the elegant studies of the Tang group whose first and asymmetric synthesis of 5 indicated that the natural product is misassigned and that the real pipercyclobutanamide A is actually the constitutionally isomeric cyclohexene containing natural product chabamide: R. Liu, M. Zhang, T. P. Wyche, G. N. Winston-McPherson, T. S. Bugni, W. Tang, Angew. Chem. 2012, DOI:; Angew. Chem. Int. Ed. 2012, DOI:.
- (2012) Angew. Chem.
- Liu, R.¹ Zhang, M.² Wyche, T.P.³ Winston-Mcpherson, G.N.⁴ Bugni, T.S.⁵ Tang, W.⁶

41
- 67650984682
- I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193-205.
- (2009) Nat. Chem. , vol.1 , pp. 193-205
- Young, I.S.¹ Baran, P.S.²

42
- 77954562085
- T. Gaich, P. S. Baran, J. Org. Chem. 2010, 75, 4657-4673.
- (2010) J. Org. Chem. , vol.75 , pp. 4657-4673
- Gaich, T.¹ Baran, P.S.²

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