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Organic and Biomolecular Chemistry

Volumn 8, Issue 5, 2010, Pages 1188-1193

Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements

(2) Black, Fiona J a Kocienski, Philip J a

a UNIVERSITY OF LEEDS (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CORE COMPONENTS; FRUITING BODIES; SCHIZOPHYLLUM COMMUNE; SPHINGOLIPIDS;

CEREBROSIDE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SCHIZOPHYLLUM; SYNTHESIS; UROCHORDATA;

ANIMALS; CEREBROSIDES; MOLECULAR STRUCTURE; SCHIZOPHYLLUM; UROCHORDATA;

ASCIDIA; ASCIDIACEA; BASIDIOMYCOTA; PHALLUSIA; SCHIZOPHYLLUM COMMUNE;

EID: 77149142270 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b920285d Document Type: Article

Times cited : (14)

References (75)

1
- 0142122853
- R. X. Tan J. H. Chen Nat. Prod. Rep. 2003 20 509
- (2003) Nat. Prod. Rep. , vol.20 , pp. 509
- Tan, R.X.¹ Chen, J.H.²

2
- 17844397203
- J. Y. Liao J. H. Tao G. Q. Lin D. G. Liu Tetrahedron 2005 61 4715
- (2005) Tetrahedron , vol.61 , pp. 4715
- Liao, J.Y.¹ Tao, J.H.² Lin, G.Q.³ Liu, D.G.⁴

3
- 0024541436
- Y. A. Hannun R. M. Bell Science 1989 243 500
- (1989) Science , vol.243 , pp. 500
- Hannun, Y.A.¹ Bell, R.M.²

4
- 0034528032
- S. Hakomori Glycoconjugate J. 2000 17 143
- (2000) Glycoconjugate J. , vol.17 , pp. 143
- Hakomori, S.¹

5
- 84900711614
- Springer, Sphingoid bases with fewer than 16 carbons have been isolated:
- T. Hirabayashi, Y. Igarashi and A. H. Merrill Jr., Sphingolipid Biology, Springer, 2006
- (2006) Sphingolipid Biology
- Hirabayashi, T.¹ Igarashi, Y.² Merrill, Jr.A.H.³

6
- 0038336141
- H. C. Kwon K. C. Lee O. R. Cho I. Y. Jung S. Y. Cho S. Y. Kim K. R. Lee J. Nat. Prod. 2003 66 466 469
- (2003) J. Nat. Prod. , vol.66 , pp. 466-469
- Kwon, H.C.¹ Lee, K.C.² Cho, O.R.³ Jung, I.Y.⁴ Cho, S.Y.⁵ Kim, S.Y.⁶ Lee, K.R.⁷

7
- 0034815559
- C. K. Savile G. Fabrias P. H. Buist J. Am. Chem. Soc. 2001 123 4382
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 4382
- Savile, C.K.¹ Fabrias, G.² Buist, P.H.³

8
- 0037007830
- C. Beckmann J. Rattke N. J. Oldham P. Sperling E. Heinz W. Boland Angew. Chem., Int. Ed. 2002 41 2298
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2298
- Beckmann, C.¹ Rattke, J.² Oldham, N.J.³ Sperling, P.⁴ Heinz, E.⁵ Boland, W.⁶

9
- 0037067746
- P. Ternes S. Franke U. Zahringer P. Sperling E. Heinz J. Biol. Chem. 2002 277 25512
- (2002) J. Biol. Chem. , vol.277 , pp. 25512
- Ternes, P.¹ Franke, S.² Zahringer, U.³ Sperling, P.⁴ Heinz, E.⁵

10
- 0035823633
- M. Leipelt D. Warnecke U. Zahringer C. Ott F. Müller B. Hube E. Heinz J. Biol. Chem. 2001 276 33621
- (2001) J. Biol. Chem. , vol.276 , pp. 33621
- Leipelt, M.¹ Warnecke, D.² Zahringer, U.³ Ott, C.⁴ Müller, F.⁵ Hube, B.⁶ Heinz, E.⁷

11
- 0038356303
- P. Sperling E. Heinz Biochim. Biophys. Acta 2003 1632 1
- (2003) Biochim. Biophys. Acta , vol.1632 , pp. 1
- Sperling, P.¹ Heinz, E.²

12
- 33646823661
- P. Ternes P. Sperling S. Albrecht S. Franke J. M. Cregg D. Warnecke E. Heinz J. Biol. Chem. 2006 281 5582
- (2006) J. Biol. Chem. , vol.281 , pp. 5582
- Ternes, P.¹ Sperling, P.² Albrecht, S.³ Franke, S.⁴ Cregg, J.M.⁵ Warnecke, D.⁶ Heinz, E.⁷

13
- 0000311544
- G. Kawai Y. Ikeda Biochim. Biophys. Acta 1982 719 612
- (1982) Biochim. Biophys. Acta , vol.719 , pp. 612
- Kawai, G.¹ Ikeda, Y.²

14
- 0018292328
- K. A. Karlsson H. Leffler B. E. Samuelsson Biochim. Biophys. Acta 1979 574 79
- (1979) Biochim. Biophys. Acta , vol.574 , pp. 79
- Karlsson, K.A.¹ Leffler, H.² Samuelsson, B.E.³

15
- 8444252968
- R. G. Shu F. W. Wang Y. M. Yang Y. X. Liu R. X. Tan Lipids 2004 39 667
- (2004) Lipids , vol.39 , pp. 667
- Shu, R.G.¹ Wang, F.W.² Yang, Y.M.³ Liu, Y.X.⁴ Tan, R.X.⁵

16
- 61349141294
- S. Zauner U. Zahringer B. Lindner D. Warnecke P. Sperling J. Biol. Chem. 2008 283 36734
- (2008) J. Biol. Chem. , vol.283 , pp. 36734
- Zauner, S.¹ Zahringer, U.² Lindner, B.³ Warnecke, D.⁴ Sperling, P.⁵

17
- 0020514241
- E. Okuyama M. Yamazaki Chem. Pharm. Bull. 1983 31 2209
- (1983) Chem. Pharm. Bull. , vol.31 , pp. 2209
- Okuyama, E.¹ Yamazaki, M.²

18
- 0025647272
- H. Shibuya K. Kawashima M. Sakagami H. Kawanishi M. Shimomura K. Ohashi I. Kitagawa Chem. Pharm. Bull. 1990 38 2933
- (1990) Chem. Pharm. Bull. , vol.38 , pp. 2933
- Shibuya, H.¹ Kawashima, K.² Sakagami, M.³ Kawanishi, H.⁴ Shimomura, M.⁵ Ohashi, K.⁶ Kitagawa, I.⁷

19
- 0027490351
- H. Shibuya M. Kurosu K. Minagawa S. Katayama I. Kitagawa Chem. Pharm. Bull. 1993 41 1534
- (1993) Chem. Pharm. Bull. , vol.41 , pp. 1534
- Shibuya, H.¹ Kurosu, M.² Minagawa, K.³ Katayama, S.⁴ Kitagawa, I.⁵

20
- 84954906549
- G. Kawai Y. Ikeda K. Tubaki Agric. Biol. Chem. 1985 49 2137
- (1985) Agric. Biol. Chem. , vol.49 , pp. 2137
- Kawai, G.¹ Ikeda, Y.² Tubaki, K.³

21
- 0032504524
- Y. Mizushina L. Hanashima T. Yamaguchi M. Takemura F. Sugawara M. Saneyoshi A. Matsukage S. Yoshida K. Sakaguchi Biochem. Biophys. Res. Commun. 1998 249 17
- (1998) Biochem. Biophys. Res. Commun. , vol.249 , pp. 17
- Mizushina, Y.¹ Hanashima, L.² Yamaguchi, T.³ Takemura, M.⁴ Sugawara, F.⁵ Saneyoshi, M.⁶ Matsukage, A.⁷ Yoshida, S.⁸ Sakaguchi, K.⁹

22
- 0028209483
- W. Jin K. L. Rinehart E. A. Jares-Erijman J. Org. Chem. 1994 59 144
- (1994) J. Org. Chem. , vol.59 , pp. 144
- Jin, W.¹ Rinehart, K.L.² Jares-Erijman, E.A.³

23
- 0028204397
- T. Natori M. Morita K. Akimoto Y. Koezuka Tetrahedron 1994 50 2771
- (1994) Tetrahedron , vol.50 , pp. 2771
- Natori, T.¹ Morita, M.² Akimoto, K.³ Koezuka, Y.⁴

24
- 0028986518
- K. Motoki E. Kobayashi T. Uchida H. Fukushima Y. Koezuka Bioorg. Med. Chem. Lett. 1995 5 705
- (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 705
- Motoki, K.¹ Kobayashi, E.² Uchida, T.³ Fukushima, H.⁴ Koezuka, Y.⁵

25
- 0032717309
- C. Curfman D. Liotta Methods Enzymol. 2000 311 391
- (2000) Methods Enzymol. , vol.311 , pp. 391
- Curfman, C.¹ Liotta, D.²

26
- 0031873509
- P. M. Koskinen A. M. P. Koskinen Synthesis 1998 1075
- (1998) Synthesis , pp. 1075
- Koskinen, P.M.¹ Koskinen, A.M.P.²

27
- 0032692343
- P. M. Koskinen A. M. P. Koskinen Methods Enzymol. 2000 311 458
- (2000) Methods Enzymol. , vol.311 , pp. 458
- Koskinen, P.M.¹ Koskinen, A.M.P.²

28
- 33644883072
- Y. Cai C.-C. Ling D. R. Bundle Org. Biomol. Chem. 2006 4 1140
- (2006) Org. Biomol. Chem. , vol.4 , pp. 1140
- Cai, Y.¹ Ling, C.-C.² Bundle, D.R.³

29
- 33744932158
- P. Merino P. Jimenez T. Tejero J. Org. Chem. 2006 71 4685
- (2006) J. Org. Chem. , vol.71 , pp. 4685
- Merino, P.¹ Jimenez, P.² Tejero, T.³

30
- 34547944244
- H. Yang L. S. Liebeskind Org. Lett. 2007 9 2993
- (2007) Org. Lett. , vol.9 , pp. 2993
- Yang, H.¹ Liebeskind, L.S.²

31
- 57049141168
- J. A. Morales-Serna J. Llaveria Y. Diaz M. I. Matheu S. Castillon Org. Biomol. Chem. 2008 6 4502
- (2008) Org. Biomol. Chem. , vol.6 , pp. 4502
- Morales-Serna, J.A.¹ Llaveria, J.² Diaz, Y.³ Matheu, M.I.⁴ Castillon, S.⁵

32
- 0000689983
- K. Mori Y. Funaki Tetrahedron 1985 41 2369
- (1985) Tetrahedron , vol.41 , pp. 2369
- Mori, K.¹ Funaki, Y.²

33
- 0001648144
- K. Mori Y. Funaki Tetrahedron 1985 41 2379
- (1985) Tetrahedron , vol.41 , pp. 2379
- Mori, K.¹ Funaki, Y.²

34
- 45249102406
- K. Mori K. Uenishi Liebigs Annalen 1996 1
- (1996) Liebigs Annalen , pp. 1
- Mori, K.¹ Uenishi, K.²

35
- 23944451799
- T. Murakami R. Hirono K. Furusawa Tetrahedron 2005 61 9233
- (2005) Tetrahedron , vol.61 , pp. 9233
- Murakami, T.¹ Hirono, R.² Furusawa, K.³

36
- 0034553059
- Y.-L. Wu X.-Z. Wang S. Jiang G. Singh J. Org. Chem. 2000 65 8146
- (2000) J. Org. Chem. , vol.65 , pp. 8146
- Wu, Y.-L.¹ Wang, X.-Z.² Jiang, S.³ Singh, G.⁴

37
- 0025318898
- A. Irie H. Kubo M. Hoshi J. Biochem. 1990 107 578
- (1990) J. Biochem. , vol.107 , pp. 578
- Irie, A.¹ Kubo, H.² Hoshi, M.³

38
- 0032569786
- R. Duran E. Zubia M. J. Ortega S. Naranjo J. Salva Tetrahedron 1998 54 14597
- (1998) Tetrahedron , vol.54 , pp. 14597
- Duran, R.¹ Zubia, E.² Ortega, M.J.³ Naranjo, S.⁴ Salva, J.⁵

39
- 0036594820
- M. E. D. de Vivar A. M. Seldes M. S. Maier Lipids 2002 37 597
- (2002) Lipids , vol.37 , pp. 597
- De Vivar, M.E.D.¹ Seldes, A.M.² Maier, M.S.³

40
- 0031842441
- M. S. Maier A. Kuriss A. M. Seldes Lipids 1998 33 825
- (1998) Lipids , vol.33 , pp. 825
- Maier, M.S.¹ Kuriss, A.² Seldes, A.M.³

41
- 0032483752
- W. Adam W. Boland J. Hartmann-Schreier H. U. Humpf M. Lazarus A. Saffert C. R. Saha-Moller P. Schreier J. Am. Chem. Soc. 1998 120 11044
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11044
- Adam, W.¹ Boland, W.² Hartmann-Schreier, J.³ Humpf, H.U.⁴ Lazarus, M.⁵ Saffert, A.⁶ Saha-Moller, C.R.⁷ Schreier, P.⁸

42
- 0032736221
- W. Adam M. Lazarus C. R. Saha-Moller P. Schreier Acc. Chem. Res. 1999 32 837
- (1999) Acc. Chem. Res. , vol.32 , pp. 837
- Adam, W.¹ Lazarus, M.² Saha-Moller, C.R.³ Schreier, P.⁴

43
- 0023490509
- M. Nakagawa S.-i. Kodato K. Nakayama T. Hino Tetrahedron Lett. 1987 28 6281
- (1987) Tetrahedron Lett. , vol.28 , pp. 6281
- Nakagawa, M.¹ K, S.-I.² Nakayama, K.³ Hino, T.⁴

44
- 0016054815
- K. A. Karlsson I. Pascher Chem. Phys. Lipids 1974 12 65
- (1974) Chem. Phys. Lipids , vol.12 , pp. 65
- Karlsson, K.A.¹ Pascher, I.²

45
- 0000366453
- T. Sugai H. Ohta Agric. Biol. Chem. 1990 54 3337
- (1990) Agric. Biol. Chem. , vol.54 , pp. 3337
- Sugai, T.¹ Ohta, H.²

46
- 0000836695
- W. Adam M. Lazarus A. Schmerder H. U. Humpf C. R. Saha-Moller P. Schreier Eur. J. Org. Chem. 1998 2013
- (1998) Eur. J. Org. Chem. , pp. 2013
- Adam, W.¹ Lazarus, M.² Schmerder, A.³ Humpf, H.U.⁴ Saha-Moller, C.R.⁵ Schreier, P.⁶

47
- 0002558905
- S. V. Pansare G. Huyer L. D. Arnold J. C. Vederas Org. Synth. 1991 70 1
- (1991) Org. Synth. , vol.70 , pp. 1
- Pansare, S.V.¹ Huyer, G.² Arnold, L.D.³ Vederas, J.C.⁴

48
- 0000059963
- J. F. Normant A. Alexakis G. Cahiez Tetrahedron Lett. 1980 21 935
- (1980) Tetrahedron Lett. , vol.21 , pp. 935
- Normant, J.F.¹ Alexakis, A.² Cahiez, G.³

49
- 0001418752
- T. Fujisawa T. Sato T. Kawara M. Kawashima H. Shimazu Y. Ito Tetrahedron Lett. 1980 21 2181
- (1980) Tetrahedron Lett. , vol.21 , pp. 2181
- Fujisawa, T.¹ Sato, T.² Kawara, T.³ Kawashima, M.⁴ Shimazu, H.⁵ Ito, Y.⁶

50
- 0000242199
- 4 at 80 °C and obtained a 58% yield of (R)-16 at the expense of a diminished ee (85%). The high temperature was required for homogeneity
- L. D. Arnold J. C. G. Drover J. C. Vederas J. Am. Chem. Soc. 1987 109 4649
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 4649
- Arnold, L.D.¹ Drover, J.C.G.² Vederas, J.C.³

51
- 0028585802
- L. Pegorier Y. Petit A. Mambu M. Larcheveque Synthesis 1994 1403
- (1994) Synthesis , pp. 1403
- Pegorier, L.¹ Petit, Y.² Mambu, A.³ Larcheveque, M.⁴

52
- 85027424616
- Y. Petit M. Larcheveque Org. Synth. 1998 75 37
- (1998) Org. Synth. , vol.75 , pp. 37
- Petit, Y.¹ Larcheveque, M.²

53
- 51949110354
- K. Jarowicki C. Kilner P. J. Kocienski Z. Komsta J. E. Milne A. Wojtasiewicz V. Coombs Synthesis 2008 2747
- (2008) Synthesis , pp. 2747
- Jarowicki, K.¹ Kilner, C.² Kocienski, P.J.³ Komsta, Z.⁴ Milne, J.E.⁵ Wojtasiewicz, A.⁶ Coombs, V.⁷

54
- 0041802763
- P. J. Kocienski C. Barber Pure Appl. Chem. 1990 62 1933
- (1990) Pure Appl. Chem. , vol.62 , pp. 1933
- Kocienski, P.J.¹ Barber, C.²

55
- 33845185013
- P. Kocienski S. Wadman K. Cooper J. Am. Chem. Soc. 1989 111 2363
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 2363
- Kocienski, P.¹ Wadman, S.² Cooper, K.³

56
- 0001050338
- P. Kocienski S. Wadman K. Cooper J. Org. Chem. 1989 54 1215
- (1989) J. Org. Chem. , vol.54 , pp. 1215
- Kocienski, P.¹ Wadman, S.² Cooper, K.³

57
- 0037034916
- J. E. Milne K. Jarowicki P. J. Kocienski J. Alonso Chem. Commun. 2002 426
- (2002) Chem. Commun. , pp. 426
- Milne, J.E.¹ Jarowicki, K.² Kocienski, P.J.³ Alonso, J.⁴

58
- 34447307671
- J. A. Morales-Serna O. Boutureira Y. Diaz M. I. Matheu S. Castillon Carbohydr. Res. 2007 342 1595
- (2007) Carbohydr. Res. , vol.342 , pp. 1595
- Morales-Serna, J.A.¹ Boutureira, O.² Diaz, Y.³ Matheu, M.I.⁴ Castillon, S.⁵

59
- 84985610035
- R. R. Schmidt P. Zimmermann Angew. Chem., Int. Ed. Engl. 1986 25 725
- (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 725
- Schmidt, R.R.¹ Zimmermann, P.²

60
- 0038399264
- S. Figueroa-Perez R. R. Schmidt Carbohydr. Res. 2000 328 95
- (2000) Carbohydr. Res. , vol.328 , pp. 95
- Figueroa-Perez, S.¹ Schmidt, R.R.²

61
- 0022636075
- R. R. Schmidt Angew. Chem., Int. Ed. Engl. 1986 25 212
- (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 212
- Schmidt, R.R.¹

62
- 0025027557
- K. D. Kim P. A. Magriotis Tetrahedron Lett. 1990 31 6137
- (1990) Tetrahedron Lett. , vol.31 , pp. 6137
- Kim, K.D.¹ Magriotis, P.A.²

63
- 0000387486
- M. Lautens P. H. M. Delanghe J. B. Goh C. H. Zhang J. Org. Chem. 1995 60 4213
- (1995) J. Org. Chem. , vol.60 , pp. 4213
- Lautens, M.¹ Delanghe, P.H.M.² Goh, J.B.³ Zhang, C.H.⁴

64
- 0002444889
- P. De Mayo, New York
- A. G. Brook and A. R. Bassindale, in Molecular Rearrangements of Organosilicon Compounds, ed., P. De Mayo, New York, 1980
- (1980) Molecular Rearrangements of Organosilicon Compounds, Ed.
- Brook, A.G.¹ Bassindale In, A.R.²

65
- 0035835953
- W. H. Moser Tetrahedron 2001 57 2065
- (2001) Tetrahedron , vol.57 , pp. 2065
- Moser, W.H.¹

66
- 0000624982
- R. West R. Lowe H. F. Stewart A. Wright J. Am. Chem. Soc. 1971 93 282
- (1971) J. Am. Chem. Soc. , vol.93 , pp. 282
- West, R.¹ Lowe, R.² Stewart, H.F.³ Wright, A.⁴

67
- 0001264816
- H. O. House C.-Y. Chu J. M. Wilkins M. J. Umen J. Org. Chem. 1975 40 1460
- (1975) J. Org. Chem. , vol.40 , pp. 1460
- House, H.O.¹ Chu, C.-Y.² Wilkins, J.M.³ Umen, M.J.⁴

68
- 0001626633
- E. Wenkert E. L. Michelotti C. S. Swindell M. Tingoli J. Org. Chem. 1984 49 4894
- (1984) J. Org. Chem. , vol.49 , pp. 4894
- Wenkert, E.¹ Michelotti, E.L.² Swindell, C.S.³ Tingoli, M.⁴

69
- 0000704333
- E. Wenkert V. F. Ferreira E. L. Michelotti M. Tingoli J. Org. Chem. 1985 50 719
- (1985) J. Org. Chem. , vol.50 , pp. 719
- Wenkert, E.¹ Ferreira, V.F.² Michelotti, E.L.³ Tingoli, M.⁴

70
- 37049078137
- P. Kocienski M. Pritchard S. Wadman R. Whitby C. Yeates J. Chem. Soc., Perkin Trans. 1 1992 3419
- (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 3419
- Kocienski, P.¹ Pritchard, M.² Wadman, S.³ Whitby, R.⁴ Yeates, C.⁵

71
- 0024340606
- P. Kocienski C. J. Love R. J. Whitby G. Costello D. A. Roberts Tetrahedron 1989 45 3839
- (1989) Tetrahedron , vol.45 , pp. 3839
- Kocienski, P.¹ Love, C.J.² Whitby, R.J.³ Costello, G.⁴ Roberts, D.A.⁵

72
- 13244295362
- Since l-xylose and d- and l-arabinose are readily available, sphingolipids from the l-erythro and the d-and l-threo series should be accessible by our route
- J. M. Gao W. M. Zhu S. Q. Zhang X. Zhang A. L. Zhang H. Chen Y. Y. Sun M. Tang Eur. J. Lipid Sci. Technol. 2004 106 815
- (2004) Eur. J. Lipid Sci. Technol. , vol.106 , pp. 815
- Gao, J.M.¹ Zhu, W.M.² Zhang, S.Q.³ Zhang, X.⁴ Zhang, A.L.⁵ Chen, H.⁶ Sun, Y.Y.⁷ Tang, M.⁸

73
- 2942752245
- P. Somfai S. Torsell Org. Biomol. Chem. 2004 2 1643
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1643
- Somfai, P.¹ Torsell, S.²

74
- 25444470542
- A. N. Rai A. Basu J. Org. Chem. 2005 70 8228
- (2005) J. Org. Chem. , vol.70 , pp. 8228
- Rai, A.N.¹ Basu, A.²

75
- 30144438606
- V. D. Chaudhari K. S. Ajish Kumar D. D. Dhavale Org. Lett. 2005 7 5805
- (2005) Org. Lett. , vol.7 , pp. 5805
- Chaudhari, V.D.¹ Ajish Kumar, K.S.² Dhavale, D.D.³

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