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Volumn 6, Issue 9, 2008, Pages 1655-1664

Asymmetric synthesis of vicinal amino alcohols: Xestoaminol C, sphinganine and sphingosine

(6) Abraham, Elin a Davies, Stephen G a Millican, Nicholas L a Nicholson, Rebecca L a Roberts, Paul M a Smith, Andrew D a

a UNIVERSITY OF OXFORD (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS: XESTOAMINOL C, SPHINGANINE AND SPHINGOSINE; ANTI-AMINOHYDROXYLATION; SPHINGANINE;

AMIDES; FUNCTIONAL GROUPS; HYDROXYLATION; OXIDATION; SYNTHESIS (CHEMICAL);

ALCOHOLS;

DRUG DERIVATIVE; FATTY ALCOHOL; SAFINGOL; SPHINGOSINE; UNCLASSIFIED DRUG; XESTOAMINOL C;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

FATTY ALCOHOLS; MOLECULAR CONFORMATION; SPHINGOSINE; STEREOISOMERISM;

EID: 42349103981 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b801357h Document Type: Article

Times cited : (94)

References (70)

1
- 0034697199
- S. C. Bergmeier Tetrahedron 2000 56 2561
- (2000) Tetrahedron , vol.56 , pp. 2561
- Bergmeier, S.C.¹

2
- 0025173142
- C. Jiménez P. Crews J. Nat. Prod. 1990 53 978
- (1990) J. Nat. Prod. , vol.53 , pp. 978
- Jiménez, C.¹ Crews, P.²

3
- 0035927207
- L. Garrido E. Zubia M. J. Ortega S. Naranjo J. Salva Tetrahedron 2001 57 4579
- (2001) Tetrahedron , vol.57 , pp. 4579
- Garrido, L.¹ Zubia, E.² Ortega, M.J.³ Naranjo, S.⁴ Salva, J.⁵

4
- 12244274338
- For a review of the synthesis of sphinganine see:
- B. Cinque L. Di Marzio C. Centi C. Di Rocco C. Riccardi M. G. Cifone Pharmacol. Res. 2003 47 421
- (2003) Pharmacol. Res. , vol.47 , pp. 421
- Cinque, B.¹ Di Marzio, L.² Centi, C.³ Di Rocco, C.⁴ Riccardi, C.⁵ Cifone, M.G.⁶

5
- 8744278061
- A. R. Howell R. C. So S. K. Richardson Tetrahedron 2004 60 11327
- (2004) Tetrahedron , vol.60 , pp. 11327
- Howell, A.R.¹ So, R.C.² Richardson, S.K.³

6
- 0031873509
- P. M. Koskinen A. M. P. Koskinen Synthesis 1998 1075
- (1998) Synthesis , pp. 1075
- Koskinen, P.M.¹ Koskinen, A.M.P.²

7
- 0036231270
- For the enantiospecific synthesis of sphinganine and/or sphingosine see:
- A. R. Howell A. J. Ndakala Curr. Org. Chem. 2002 6 365
- (2002) Curr. Org. Chem. , vol.6 , pp. 365
- Howell, A.R.¹ Ndakala, A.J.²

8
- 0034596034
- H. Azuma S. Tamagaki K. Ogino J. Org. Chem. 2000 65 3538
- (2000) J. Org. Chem. , vol.65 , pp. 3538
- Azuma, H.¹ Tamagaki, S.² Ogino, K.³

9
- 0034926817
- R. I. Duclos Chem. Phys. Lipids 2001 111 111
- (2001) Chem. Phys. Lipids , vol.111 , pp. 111
- Duclos, R.I.¹

10
- 0035968851
- T. Nakamura M. Shiozaki Tetrahedron 2001 57 9087
- (2001) Tetrahedron , vol.57 , pp. 9087
- Nakamura, T.¹ Shiozaki, M.²

11
- 0037074113
- J. Chun G. Li H.-S. Byun R. Bittman Tetrahedron Lett. 2002 43 375
- (2002) Tetrahedron Lett. , vol.43 , pp. 375
- Chun, J.¹ Li, G.² Byun, H.-S.³ Bittman, R.⁴

12
- 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

13
- 0037155732
- J.-M. Lee H.-S. Lim S.-K. Chung Tetrahedron: Asymmetry 2002 13 343
- (2002) Tetrahedron: Asymmetry , vol.13 , pp. 343
- Lee, J.-M.¹ Lim, H.-S.² Chung, S.-K.³

14
- 0037064401
- R. J. B. H. N. van den Berg C. G. N. Korevaar G. A. van der Marel H. S. Overkleeft J. H. van Boom Tetrahedron Lett. 2002 43 8409
- (2002) Tetrahedron Lett. , vol.43 , pp. 8409
- Van Den Berg, R.J.B.H.N.¹ Korevaar, C.G.N.² Van Der Marel, G.A.³ Overkleeft, H.S.⁴ Van Boom, J.H.⁵

15
- 0037020816
- T. Murakami K. Furusawa Tetrahedron 2002 58 9257
- (2002) Tetrahedron , vol.58 , pp. 9257
- Murakami, T.¹ Furusawa, K.²

16
- 0037164689
- H. K. Lee E.-K. Kim C. S. Pak Tetrahedron Lett. 2002 43 9641
- (2002) Tetrahedron Lett. , vol.43 , pp. 9641
- Lee, H.K.¹ Kim, E.-K.² Pak, C.S.³

17
- 0038645397
- S. Raghavan A. Rajender J. S. Yadav Tetrahedron: Asymmetry 2003 14 2093
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2093
- Raghavan, S.¹ Rajender, A.² Yadav, J.S.³

18
- 0041837315
- S. Raghavan A. Rajender J. Org. Chem. 2003 68 7094
- (2003) J. Org. Chem. , vol.68 , pp. 7094
- Raghavan, S.¹ Rajender, A.²

19
- 2142653546
- R. C. So R. Ndonye D. P. Izmirian S. K. Richardson R. L. Guerra A. R. Howell J. Org. Chem. 2004 69 3233
- (2004) J. Org. Chem. , vol.69 , pp. 3233
- So, R.C.¹ Ndonye, R.² Izmirian, D.P.³ Richardson, S.K.⁴ Guerra, R.L.⁵ Howell, A.R.⁶

20
- 3543011977
- X. Lu H.-S. Byun R. Bittman J. Org. Chem. 2004 69 5433
- (2004) J. Org. Chem. , vol.69 , pp. 5433
- Lu, X.¹ Byun, H.-S.² Bittman, R.³

21
- 4043175402
- R. J. B. H. N. van den Berg C. G. N. Korevaar H. S. Overkleeft G. A. van der Marel J. H. van Boom J. Org. Chem. 2004 69 5699
- (2004) J. Org. Chem. , vol.69 , pp. 5699
- Van Den Berg, R.J.B.H.N.¹ Korevaar, C.G.N.² Overkleeft, H.S.³ Van Der Marel, G.A.⁴ Van Boom, J.H.⁵

22
- 42349105378
- M. Shimizu H. Ando Y. Niwa Lett. Org. Chem. 2005 2 512
- (2005) Lett. Org. Chem. , vol.2 , pp. 512
- Shimizu, M.¹ Ando, H.² Niwa, Y.³

23
- 13944283368
- W. Lu R. Bittman Tetrahedron Lett. 2005 46 1873
- (2005) Tetrahedron Lett. , vol.46 , pp. 1873
- Lu, W.¹ Bittman, R.²

24
- 30144438606
- V. D. Chaudhari K. S. A. Kumar D. D. Dhavale Org. Lett. 2005 7 5805
- (2005) Org. Lett. , vol.7 , pp. 5805
- Chaudhari, V.D.¹ Kumar, K.S.A.² Dhavale, D.D.³

25
- 33746876672
- M. G. Capdevila F. Pasi C. Trombini Org. Lett. 2006 8 3303
- (2006) Org. Lett. , vol.8 , pp. 3303
- Capdevila, M.G.¹ Pasi, F.² Trombini, C.³

26
- 33744932158
- P. Merino P. Jiminez T. Tejero J. Org. Chem. 2006 71 4685
- (2006) J. Org. Chem. , vol.71 , pp. 4685
- Merino, P.¹ Jiminez, P.² Tejero, T.³

27
- 33750465556
- S. Kim S. Lee T. Lee H. Ko D. Kim J. Org. Chem. 2006 71 8661
- (2006) J. Org. Chem. , vol.71 , pp. 8661
- Kim, S.¹ Lee, S.² Lee, T.³ Ko, H.⁴ Kim, D.⁵

28
- 33846023340
- T. Yamamoto H. Hasegawa T. Hakogi S. Katsumura Org. Lett. 2006 8 5569
- (2006) Org. Lett. , vol.8 , pp. 5569
- Yamamoto, T.¹ Hasegawa, H.² Hakogi, T.³ Katsumura, S.⁴

29
- 33846813433
- V.-T. Pham J.-E. Joo Y.-S. Tian C.-Y. Oh W.-H. Ham Arch. Pharmacol. Res. 2007 30 22
- (2007) Arch. Pharmacol. Res. , vol.30 , pp. 22
- Pham, V.-T.¹ Joo, J.-E.² Tian, Y.-S.³ Oh, C.-Y.⁴ Ham, W.-H.⁵

30
- 33845666640
- M. Lombardo A. Sharma S. Gamre S. Chattopadhyay Tetrahedron Lett. 2007 48 633
- (2007) Tetrahedron Lett. , vol.48 , pp. 633
- Lombardo, M.¹ Sharma, A.² Gamre, S.³ Chattopadhyay, S.⁴

31
- 33947157606
- Y. S. Tian J.-E. Joo V.-T. Pham K.-Y. Lee W.-H. Ham Arch. Pharmacol. Res. 2007 30 167
- (2007) Arch. Pharmacol. Res. , vol.30 , pp. 167
- Tian, Y.S.¹ Joo, J.-E.² Pham, V.-T.³ Lee, K.-Y.⁴ Ham, W.-H.⁵

32
- 34548669388
- A. S. Kale P. S. Sakle V. K. Gumaste A. Rakeeb A. S. Deshmukh Synthesis 2007 2631
- (2007) Synthesis , pp. 2631
- Kale, A.S.¹ Sakle, P.S.² Gumaste, V.K.³ Rakeeb, A.⁴ Deshmukh, A.S.⁵

33
- 34547944244
- For the asymmetric synthesis of sphinganine and/or sphingosine see:
- H. Yang L. S. Liebeskind Org. Lett. 2007 9 2993
- (2007) Org. Lett. , vol.9 , pp. 2993
- Yang, H.¹ Liebeskind, L.S.²

34
- 0034655861
- E. J. Corey S. Choi Tetrahedron Lett. 2000 41 2765
- (2000) Tetrahedron Lett. , vol.41 , pp. 2765
- Corey, E.J.¹ Choi, S.²

35
- 0037459676
- B. Olofsson P. Somfai J. Org. Chem. 2003 68 2514
- (2003) J. Org. Chem. , vol.68 , pp. 2514
- Olofsson, B.¹ Somfai, P.²

36
- 2942752245
- S. Torssell P. Somfai Org. Biomol. Chem. 2004 2 1643
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1643
- Torssell, S.¹ Somfai, P.²

37
- 3342953528
- J. Kobayashi M. Nakamura Y. Mori Y. Yamashita S. Kobayashi J. Am. Chem. Soc. 2004 126 9192
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 9192
- Kobayashi, J.¹ Nakamura, M.² Mori, Y.³ Yamashita, Y.⁴ Kobayashi, S.⁵

38
- 4544252293
- D. Enders A. Müller-Hüwen Eur. J. Org. Chem. 2004 1732
- (2004) Eur. J. Org. Chem. , pp. 1732
- Enders, D.¹ Müller-Hüwen, A.²

39
- 27744483875
- W. Disadee T. Ishikawa J. Org. Chem. 2005 70 9399
- (2005) J. Org. Chem. , vol.70 , pp. 9399
- Disadee, W.¹ Ishikawa, T.²

40
- 33646045013
- D. Enders J. Paleček C. Grondal Chem. Commun. 2006 655
- (2006) Chem. Commun. , pp. 655
- Enders, D.¹ Paleček, J.² Grondal, C.³

41
- 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

42
- 33750630401
- For a review see:
- G. Righi S. Ciambrone C. D'Achille A. Leonelli C. Bonini Tetrahedron 2006 62 11821
- (2006) Tetrahedron , vol.62 , pp. 11821
- Righi, G.¹ Ciambrone, S.² D'Achille, C.³ Leonelli, A.⁴ Bonini, C.⁵

43
- 24344501374
- S. G. Davies A. D. Smith P. D. Price Tetrahedron: Asymmetry 2005 16 2833
- (2005) Tetrahedron: Asymmetry , vol.16 , pp. 2833
- Davies, S.G.¹ Smith, A.D.² Price, P.D.³

44
- 37049079385
- M. E. Bunnage A. N. Chernega S. G. Davies C. J. Goodwin J. Chem. Soc., Perkin Trans. 1 1994 2373
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2373
- Bunnage, M.E.¹ Chernega, A.N.² Davies, S.G.³ Goodwin, C.J.⁴

45
- 84988114394
- M. E. Bunnage S. G. Davies C. J. Goodwin Synlett 1993 731
- (1993) Synlett , pp. 731
- Bunnage, M.E.¹ Davies, S.G.² Goodwin, C.J.³

46
- 37049075881
- M. E. Bunnage S. G. Davies C. J. Goodwin J. Chem. Soc., Perkin Trans. 1 1993 1375
- (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 1375
- Bunnage, M.E.¹ Davies, S.G.² Goodwin, C.J.³

47
- 0028196580
- M. E. Bunnage A. J. Burke S. G. Davies C. J. Goodwin Tetrahedron: Asymmetry 1994 5 203
- (1994) Tetrahedron: Asymmetry , vol.5 , pp. 203
- Bunnage, M.E.¹ Burke, A.J.² Davies, S.G.³ Goodwin, C.J.⁴

48
- 37049087129
- M. E. Bunnage S. G. Davies C. J. Goodwin J. Chem. Soc., Perkin Trans. 1 1994 2385
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2385
- Bunnage, M.E.¹ Davies, S.G.² Goodwin, C.J.³

49
- 0028860079
- M. E. Bunnage A. J. Burke S. G. Davies C. J. Goodwin Tetrahedron: Asymmetry 1995 6 165
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 165
- Bunnage, M.E.¹ Burke, A.J.² Davies, S.G.³ Goodwin, C.J.⁴

50
- 0001071709
- A. J. Burke S. G. Davies C. J. R. Hedgecock Synlett 1996 621
- (1996) Synlett , pp. 621
- Burke, A.J.¹ Davies, S.G.² Hedgecock, C.J.R.³

51
- 0344118919
- M. E. Bunnage A. J. Burke S. G. Davies N. L. Millican R. L. Nicholson P. M. Roberts A. D. Smith Org. Biomol. Chem. 2003 1 3708
- (2003) Org. Biomol. Chem. , vol.1 , pp. 3708
- Bunnage, M.E.¹ Burke, A.J.² Davies, S.G.³ Millican, N.L.⁴ Nicholson, R.L.⁵ Roberts, P.M.⁶ Smith, A.D.⁷

52
- 2942644316
- S. G. Davies D. G. Hughes R. L. Nicholson A. D. Smith A. J. Wright Org. Biomol. Chem. 2004 2 1549
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1549
- Davies, S.G.¹ Hughes, D.G.² Nicholson, R.L.³ Smith, A.D.⁴ Wright, A.J.⁵

53
- 36148970785
- E. Abraham J. I. Candela-Lena S. G. Davies M. Georgiou R. L. Nicholson P. M. Roberts A. J. Russell E. M. Sánchez-Fernández A. D. Smith J. E. Thomson Tetrahedron: Asymmetry 2007 18 2510
- (2007) Tetrahedron: Asymmetry , vol.18 , pp. 2510
- Abraham, E.¹ Candela-Lena, J.I.² Davies, S.G.³ Georgiou, M.⁴ Nicholson, R.L.⁵ Roberts, P.M.⁶ Russell, A.J.⁷ Sánchez-Fernández, E.M.⁸ Smith, A.D.⁹ Thomson, J.E.¹⁰

54
- 0041626169
- 19F NMR spectroscopy; see
- M. Ichihashi K. Mori Biosci., Biotechnol., Biochem. 2002 67 329
- (2002) Biosci., Biotechnol., Biochem. , vol.67 , pp. 329
- Ichihashi, M.¹ Mori, K.²

55
- 0010640653
- Aldehyde 13 was partially characterised and used immediately
- J. A. Dale D. L. Dull H. S. Mosher J. Org. Chem. 1969 34 2543
- (1969) J. Org. Chem. , vol.34 , pp. 2543
- Dale, J.A.¹ Dull, D.L.² Mosher, H.S.³

56
- 0034719260
- T. J. Wilkinson N. W. Stehle P. Beak Org. Lett. 2000 2 155
- (2000) Org. Lett. , vol.2 , pp. 155
- Wilkinson, T.J.¹ Stehle, N.W.² Beak, P.³

57
- 34547155602
- S. G. Davies A. W. Mulvaney A. J. Russell A. D. Smith Tetrahedron: Asymmetry 2007 18 1554
- (2007) Tetrahedron: Asymmetry , vol.18 , pp. 1554
- Davies, S.G.¹ Mulvaney, A.W.² Russell, A.J.³ Smith, A.D.⁴

58
- 0032427086
- A. D. Campbell T. M. Raynham R. J. K. Taylor Synthesis 1998 1707
- (1998) Synthesis , pp. 1707
- Campbell, A.D.¹ Raynham, T.M.² Taylor, R.J.K.³

59
- 0027988788
- M. Frigerio M. Santagostino Tetrahedron Lett. 1994 35 8019
- (1994) Tetrahedron Lett. , vol.35 , pp. 8019
- Frigerio, M.¹ Santagostino, M.²

60
- 0000295212
- IBX was prepared from 2-iodobenzoic acid according to the procedure of
- M. Frigerio M. Santagostino S. Sputore G. Palmesano J. Org. Chem. 1995 60 7272.
- (1995) J. Org. Chem. , vol.60 , pp. 7272
- Frigerio, M.¹ Santagostino, M.² Sputore, S.³ Palmesano, G.⁴

61
- 0033546262
- Aldehyde 20 was partially characterised and used immediately
- M. Frigerio M. Santagostino S. Sputore J. Org. Chem. 1999 64 4537
- (1999) J. Org. Chem. , vol.64 , pp. 4537
- Frigerio, M.¹ Santagostino, M.² Sputore, S.³

62
- 0027511770
- M. Jayaraman M. Nandi K. M. Sathe A. R. A. S. Deshmukh B. M. Bhawal Tetrahedron: Asymmetry 1993 4 609
- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 609
- Jayaraman, M.¹ Nandi, M.² Sathe, K.M.³ Deshmukh, A.R.A.S.⁴ Bhawal, B.M.⁵

63
- 34249022730
- E. Abraham J. W. B. Cooke S. G. Davies A. Naylor R. L. Nicholson P. D. Price A. D. Smith Tetrahedron 2007 63 5855
- (2007) Tetrahedron , vol.63 , pp. 5855
- Abraham, E.¹ Cooke, J.W.B.² Davies, S.G.³ Naylor, A.⁴ Nicholson, R.L.⁵ Price, P.D.⁶ Smith, A.D.⁷

64
- 84981772814
- M. Schlosser K. F. Christman Angew. Chem., Int. Ed. Engl. 1966 5 126
- (1966) Angew. Chem., Int. Ed. Engl. , vol.5 , pp. 126
- Schlosser, M.¹ Christman, K.F.²

65
- 1942504322
- J. S. Oh B. H. Kim Y. G. Kim Tetrahedron Lett. 2004 45 3925
- (2004) Tetrahedron Lett. , vol.45 , pp. 3925
- Oh, J.S.¹ Kim, B.H.² Kim, Y.G.³

66
- 0343785054
- H. E. Carter D. Shapiro J. Am. Chem. Soc. 1953 75 5131
- (1953) J. Am. Chem. Soc. , vol.75 , pp. 5131
- Carter, H.E.¹ Shapiro, D.²

67
- 0033370162
- R. A. Fernandes P. Kumar Tetrahedron: Asymmetry 1999 10 4797
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 4797
- Fernandes, R.A.¹ Kumar, P.²

68
- 0026776987
- H. Shibuya K. Kawashima N. Narita M. Ikeda I. Kitagawa Chem. Pharm. Bull. 1992 40 1154
- (1992) Chem. Pharm. Bull. , vol.40 , pp. 1154
- Shibuya, H.¹ Kawashima, K.² Narita, N.³ Ikeda, M.⁴ Kitagawa, I.⁵

69
- 27744483875
- W. Disadee T. Ishikawa J. Org. Chem. 2005 70 9399
- (2005) J. Org. Chem. , vol.70 , pp. 9399
- Disadee, W.¹ Ishikawa, T.²

70
- 5244370033
- A. B. Pangborn M. A. Giardello R. H. Grubbs R. K. Rosen F. J. Timmers Organometallics 1996 15 1518
- (1996) Organometallics , vol.15 , pp. 1518
- Pangborn, A.B.¹ Giardello, M.A.² Grubbs, R.H.³ Rosen, R.K.⁴ Timmers, F.J.⁵

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