SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 6728-6742

Study of the total synthesis of (-)-exiguolide

(4) Cook, Cyril a Liron, Frédéric a Guinchard, Xavier a Roulland, Emmanuel a

a CNRS (France)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLINGS; ENE-YNE; LITHIUM ACETYLIDES; TOTAL SYNTHESIS; WEINREB AMIDES;

AMIDES; LITHIUM;

ADDITION REACTIONS;

ACRYLIC ACID METHYL ESTER; AMIDE; EXIGUOLIDE; LITHIUM; LITHIUM ACETYLIDE; MACROLIDE; PALLADIUM; TETRAHYDROPYRANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; HORNER WADSWORTH EMMONS REACTION; MICHAEL ADDITION; SUBSTITUTION REACTION; SYNTHESIS;

ACRYLATES; AMIDES; CATALYSIS; LITHIUM; MACROLIDES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 84865254740 PISSN: 00223263 EISSN: 15206904 Source Type: Journal
DOI: 10.1021/jo301066p Document Type: Article

Times cited : (27)

References (46)

1
- 32644465227
- Ohta, S.; Uy, M. M.; Yanai, M.; Ohta, E.; Hirata, T.; Ikegami, S. Tetrahedron Lett. 2006, 47, 1957-1960
- (2006) Tetrahedron Lett. , vol.47 , pp. 1957-1960
- Ohta, S.¹ Uy, M.M.² Yanai, M.³ Ohta, E.⁴ Hirata, T.⁵ Ikegami, S.⁶

2
- 80052828252
- Crane, E. A.; Zabawa, T. P.; Farmer, R. L.; Scheidt, K. A. Angew. Chem., Int. Ed. 2011, 50, 9112-9115
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 9112-9115
- Crane, E.A.¹ Zabawa, T.P.² Farmer, R.L.³ Scheidt, K.A.⁴

3
- 0028021743
- Ikegami, S.; Kobayashi, H.; Myotoishi, Y.; Ohto, S.; Kato, K. H. J. Biol. Chem. 1994, 269, 23262-23267
- (1994) J. Biol. Chem. , vol.269 , pp. 23262-23267
- Ikegami, S.¹ Kobayashi, H.² Myotoishi, Y.³ Ohto, S.⁴ Kato, K.H.⁵

4
- 79951787873
- Fuwa, H.; Suzuki, T.; Kubo, H.; Yamori, T.; Sasaki, M. Chem.-Eur. J. 2011, 17, 2678-2688
- (2011) Chem.-Eur. J. , vol.17 , pp. 2678-2688
- Fuwa, H.¹ Suzuki, T.² Kubo, H.³ Yamori, T.⁴ Sasaki, M.⁵

5
- 77957607384
- Reddy, C. R.; Rao, N. N. Tetrahedron Lett. 2010, 51, 5840-5842
- (2010) Tetrahedron Lett. , vol.51 , pp. 5840-5842
- Reddy, C.R.¹ Rao, N.N.²

6
- 41049112894
- Kwon, M. S.; Woo, S. K.; Na, S. W.; Lee, E. Angew. Chem., Int. Ed. 2008, 47, 1733-1735
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 1733-1735
- Kwon, M.S.¹ Woo, S.K.² Na, S.W.³ Lee, E.⁴

7
- 76849105782
- Cook, C.; Guinchard, X.; Liron, F.; Roulland, E. Org. Lett. 2010, 12, 744-747
- (2010) Org. Lett. , vol.12 , pp. 744-747
- Cook, C.¹ Guinchard, X.² Liron, F.³ Roulland, E.⁴

8
- 75749158496
- Fuwa, H.; Sasaki, M. Org. Lett. 2010, 12, 584-587
- (2010) Org. Lett. , vol.12 , pp. 584-587
- Fuwa, H.¹ Sasaki, M.²

9
- 27544502994
- Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630-6666
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6630-6666
- Trost, B.M.¹ Frederiksen, M.U.² Rudd, M.T.³

10
- 84943704894
- Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Marthre, D. J.; Bartroli J. Pure Appl. Chem. 1981, 53, 1109-1027
- (1981) J. Pure Appl. Chem. , vol.53 , pp. 1109-1027
- Evans, D.A.¹ Takacs, J.M.² McGee, L.R.³ Ennis, M.D.⁴ Marthre, D.J.⁵ Bartroli, J.⁶

11
- 0742286900
- Paquette, W. D.; Taylor, R. E. Org. Lett. 2004, 6, 103-106
- (2004) Org. Lett. , vol.6 , pp. 103-106
- Paquette, W.D.¹ Taylor, R.E.²

12
- 0242330782
- Evans, D. A.; Starr, J. T. J. Am. Chem. Soc. 2003, 125, 13531-13540
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 13531-13540
- Evans, D.A.¹ Starr, J.T.²

13
- 33845559983
- Gemal, A. L.; Luche, J. L. J. Org. Chem. 1979, 44, 4187-4189
- (1979) J. Org. Chem. , vol.44 , pp. 4187-4189
- Gemal, A.L.¹ Luche, J.L.²

14
- 84958682784
- Lindlar, H. Helv. Chim. Acta 1952, 35, 446
- (1952) Helv. Chim. Acta , vol.35 , pp. 446
- Lindlar, H.¹

15
- 0000340426
- Lindlar, H.; Dubuis, R. Org. Synth. 1973, V, 880
- (1973) Org. Synth. , vol.5 , pp. 880
- Lindlar, H.¹ Dubuis, R.²

16
- 0141630613
- Harrington-Frost, N.; Leuser, H.; Calaza, M. I.; Kneisel, F. F.; Knochel, P. Org. Lett. 2003, 5, 2111-2114
- (2003) Org. Lett. , vol.5 , pp. 2111-2114
- Harrington-Frost, N.¹ Leuser, H.² Calaza, M.I.³ Kneisel, F.F.⁴ Knochel, P.⁵

17
- 33750026643
- Negishi, E.-i. Acc. Chem. Res. 2002, 15, 340-348
- (2002) Acc. Chem. Res. , vol.15 , pp. 340-348
- Negishi, E.-I.¹

18
- 33644955826
- Liang, B.; Novak, T.; Tan, Z.; Negishi, E.-i. J. Am. Chem. Soc. 2006, 128, 2770-2771
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 2770-2771
- Liang, B.¹ Novak, T.² Tan, Z.³

19
- 20444438358
- Roulland, E.; Ermolenko, M. S. Org. Lett. 2005, 7, 2225-2228
- (2005) Org. Lett. , vol.7 , pp. 2225-2228
- Roulland, E.¹ Ermolenko, M.S.²

20
- 0030860279
- Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 936-938
- (1997) Science , pp. 936-938
- Tokunaga, M.¹ Larrow, J.F.² Kakiuchi, F.³ Jacobsen, E.N.⁴

21
- 26844539912
- Enholm, E.; Joshi, A.; Wright, D. L. Bioorg. Med. Chem. Lett. 2005, 15, 5262
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 5262
- Enholm, E.¹ Joshi, A.² Wright, D.L.³

22
- 12644312578
- Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482
- (1978) J. Org. Chem. , vol.43 , pp. 2480-2482
- Mancuso, A.J.¹ Huang, S.-L.² Swern, D.³

23
- 32744459401
- Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660
- (1978) Tetrahedron , vol.34 , pp. 1651-1660
- Omura, K.¹ Swern, D.²

24
- 33845377368
- Petrier, C.; Luche, J. L. J. Org. Chem. 1985, 50, 910-912
- (1985) J. Org. Chem. , vol.50 , pp. 910-912
- Petrier, C.¹ Luche, J.L.²

25
- 0033556593
- Ramachandran, P. V.; Krzeminski, M. P.; Ram Reddy, M. V.; Brown, H. C. Tetrahedron: Asymmetry 1999, 10, 11
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 11
- Ramachandran, P.V.¹ Krzeminski, M.P.² Ram Reddy, M.V.³ Brown, H.C.⁴

26
- 33748238456
- Tamaru, Y.; Yasui, K.; Takanabe, H.; Tanaka, S.; Fugami, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 645
- (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 645
- Tamaru, Y.¹ Yasui, K.² Takanabe, H.³ Tanaka, S.⁴ Fugami, K.⁵

27
- 0027327707
- Wilk, B. K. Synth. Commun. 1993, 23, 2481-2484
- (1993) Synth. Commun. , vol.23 , pp. 2481-2484
- Wilk, B.K.¹

28
- 25444517747
- Zhang, W.; Carter, R. G. Org. Lett. 2005, 7, 4209-4212
- (2005) Org. Lett. , vol.7 , pp. 4209-4212
- Zhang, W.¹ Carter, R.G.²

29
- 33845374534
- Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439
- (1986) J. Org. Chem. , vol.51 , pp. 432-439
- Jadhav, P.K.¹ Bhat, K.S.² Perumal, P.T.³ Brown, H.C.⁴

30
- 0001092074
- Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156-4158
- (1983) J. Org. Chem. , vol.48 , pp. 4156-4158
- Dess, D.B.¹ Martin, J.C.²

31
- 3042741556
- Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 7277-7287
- Dess, D.B.¹ Martin, J.C.²

32
- 3042744115
- Funel, J.-A.; Prunet, J. J. Org. Chem. 2004, 69, 4555-4558
- (2004) J. Org. Chem. , vol.69 , pp. 4555-4558
- Funel, J.-A.¹ Prunet, J.²

33
- 0026678562
- Kabat, M. M.; Lange, M.; Wovkulich, P. M.; Uskoković, M. R. Tetrahedron Lett. 1992, 33, 7701-7704
- (1992) Tetrahedron Lett. , vol.33 , pp. 7701-7704
- Kabat, M.M.¹ Lange, M.² Wovkulich, P.M.³ Uskoković, M.R.⁴

34
- 0038202225
- Shen, R.; Lin, C. T.; Bowman, E. J.; Bowman, B. J.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 7889-7901
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 7889-7901
- Shen, R.¹ Lin, C.T.² Bowman, E.J.³ Bowman, B.J.⁴ Porco Jr., J.A.⁵

35
- 0000426192
- Ozeki, T.; Kusaka, M. Bull. Chem. Soc. Jpn. 1966, 39, 1995-1998
- (1966) Bull. Chem. Soc. Jpn. , vol.39 , pp. 1995-1998
- Ozeki, T.¹ Kusaka, M.²

36
- 20444438358
- Roulland, E.; Ermolenko, M. S. Org. Lett. 2005, 7, 2225-2228
- (2005) Org. Lett. , vol.7 , pp. 2225-2228
- Roulland, E.¹ Ermolenko, M.S.²

37
- 0038800280
- Larchevêque, M.; Petit, Y. Bull. Chim. Soc. Fr. 1989, 130-139
- (1989) Bull. Chim. Soc. Fr. , pp. 130-139
- Larchevêque, M.¹ Petit, Y.²

38
- 0001681767
- Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318-3326
- (1974) J. Org. Chem. , vol.39 , pp. 3318-3326
- Schoenberg, A.¹ Bartoletti, I.² Heck, R.F.³

39
- 0001616071
- Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993
- (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 1989-1993
- Inanaga, J.¹ Hirata, K.² Saeki, H.³ Katsuki, T.⁴ Yamaguchi, M.⁵

40
- 0043194171
- Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 11360-11370
- Chatterjee, A.K.¹ Choi, T.-L.² Sanders, D.P.³ Grubbs, R.H.⁴

41
- 62049085616
- Uno, B. E.; Gillis, E. P.; Burke, M. D. Tetrahedron 2009, 6, 3130-3138
- (2009) Tetrahedron , vol.6 , pp. 3130-3138
- Uno, B.E.¹ Gillis, E.P.² Burke, M.D.³

42
- 0001446768
- Kujawa-Welten, M.; Pietraszuk, C.; Marciniec, B. Organometallics 2002, 21, 840-845
- (2002) Organometallics , vol.21 , pp. 840-845
- Kujawa-Welten, M.¹ Pietraszuk, C.² Marciniec, B.³

43
- 0001654231
- Schroeder, M. Chem. Rev. 1980, 80, 187-213
- (1980) Chem. Rev. , vol.80 , pp. 187-213
- Schroeder, M.¹

44
- 0003757056
- In; Wiberg, K. Academic: New York
- Bunton, C. A. In Oxidation in Organic Chemistry, Part A; Wiberg, K., Ed.; Academic: New York, 1965; pp 398-405.
- (1965) Oxidation in Organic Chemistry, Part A , pp. 398-405
- Bunton, C.A.¹

45
- 33845373603
- Takai, K.; Nitta, K.; Utimoto, K. 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

46
- 0141739284
- For the synthesis of the precursor of 72, see
- For the synthesis of the precursor of 72, see: Kigoshi, H.; Kita, M.; Ogawa, S.; Itoh, M.; Uemura, D. Org. Lett. 2003, 5, 957-960
- (2003) Org. Lett. , vol.5 , pp. 957-960
- Kigoshi, H.¹ Kita, M.² Ogawa, S.³ Itoh, M.⁴ Uemura, D.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.