Lobocyclamide B from Lyngbya confervoides. Configuration and Asymmetric Synthesis of β-Hydroxy-α-amino Acids by (-)-Sparteine-Mediated Aldol Addition

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1883-1886

  MacMillan, John B ^a   Molinski, Tadeusz F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANTIFUNGAL AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LITHIUM; SPARTEINE;

ARTICLE; CHEMISTRY; CONFORMATION; CYANOBACTERIUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; OPTICAL ROTATION;

AMINO ACIDS; ANTIBIOTICS, ANTIFUNGAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYANOBACTERIA; INDICATORS AND REAGENTS; LITHIUM; MOLECULAR CONFORMATION; OPTICAL ROTATION; SPARTEINE;

EID: 0037198776     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025876k     Document Type: Article

References (42)

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2. For recent examples, see: (a) Williams, P. G.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2002, 65(1), 29-31. (b) Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2002, 65(1), 16-20. For a recent review, see: (c) Gerwick, W. H.; Tan, L. T.; Sitachitta, N. In The Alkaloids, Vol. 57; Cordell, G. A., Ed.; Academic Press: San Diego, 2001; pp 75-184.
3. For recent examples, see: (a) Williams, P. G.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2002, 65(1), 29-31. (b) Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2002, 65(1), 16-20. For a recent review, see: (c) Gerwick, W. H.; Tan, L. T.; Sitachitta, N. In The Alkaloids, Vol. 57; Cordell, G. A., Ed.; Academic Press: San Diego, 2001; pp 75-184.
4. Partly presented: Ernst-Russell, M. A.; Molinski, T. F. 36th Western Regional Meeting of the American Chemical Society, San Francisco, CA, October 2000.
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12. 4
13. Optical purities of all purified threo and erythro diastereomers were determined by chiral HPLC (Chiral Pak OD column, 1-2.5% i-PrOH: hexanes, UV and evaporative light scattering detectors).
14. Jung, M. E.; Jung, Y. H. Tetrahedron Lett 1989, 48, 6637-6640.
15. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
16. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
17. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
18. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
19. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
20. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
21. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
22. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
23. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
24. For recent syntheses of β-hydroxyleucine stereoisomers, see: (a) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymmetry 2001, 12, 563-569. (b) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666. (c) Laib, T.; Chastanet, J.; Zhu, J. P. J. Org. Chem. 1998, 63, 1709-1713. (d) Laib, T.; Chastanet, J.; Zhu, J. P. Tetrahedron Lett. 1997, 38, 1771-1772. (e) Williams, L.; Zhang, Z. D.; Ding, X. B.; Joullie, M. M. Tetrahedron Lett. 1995, 36, 7031-7034. (f) Yadav, J. S.; Chandrasekhar, S.; Reddy, Y. R.; Rao, A. V. R. Tetrahedron 1995, 51, 2749-2754. (g) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (h) Corey, E. J.; Lee, D. H.; Choi, S. Y. Tetrahedron Lett. 1992, 33, 6735-6738. (i) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34-36. (j) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
25. 2, MeOH) gave the γ-hydroxythreonine diastereomers (2S,3S)-(-)-2-amino-3,4-dihydroxybutyric acid and (2R,3S)-(+)-2-amino-3,4-dihydroxybutyric acid, respectively. For a synthesis of the enantiomer of the latter compound, see: Pirrung, M. C.; Nunn, D. S.; McPhail, A. T.; Mitchell, R. E. Bioorg. Med. Chem. Lett. 1993, 3, 2095-2098. For the definitive configurational assignments of β-hydroxythreonine stereoisomers, see: Hamel, E. E.; Painter, E. P. J. Am. Chem. Soc. 1953, 75, 1362-1368. Niemann, C.; Nichols, P. L. J Biol. Chem. 1942, 143, 191-199.
26. 2, MeOH) gave the γ-hydroxythreonine diastereomers (2S,3S)-(-)-2-amino-3,4-dihydroxybutyric acid and (2R,3S)-(+)-2-amino-3,4-dihydroxybutyric acid, respectively. For a synthesis of the enantiomer of the latter compound, see: Pirrung, M. C.; Nunn, D. S.; McPhail, A. T.; Mitchell, R. E. Bioorg. Med. Chem. Lett. 1993, 3, 2095-2098. For the definitive configurational assignments of β-hydroxythreonine stereoisomers, see: Hamel, E. E.; Painter, E. P. J. Am. Chem. Soc. 1953, 75, 1362-1368. Niemann, C.; Nichols, P. L. J Biol. Chem. 1942, 143, 191-199.
27. 2, MeOH) gave the γ-hydroxythreonine diastereomers (2S,3S)-(-)-2-amino-3,4-dihydroxybutyric acid and (2R,3S)-(+)-2-amino-3,4-dihydroxybutyric acid, respectively. For a synthesis of the enantiomer of the latter compound, see: Pirrung, M. C.; Nunn, D. S.; McPhail, A. T.; Mitchell, R. E. Bioorg. Med. Chem. Lett. 1993, 3, 2095-2098. For the definitive configurational assignments of β-hydroxythreonine stereoisomers, see: Hamel, E. E.; Painter, E. P. J. Am. Chem. Soc. 1953, 75, 1362-1368. Niemann, C.; Nichols, P. L. J Biol. Chem. 1942, 143, 191-199.
28. 2, MeOH) gave the γ-hydroxythreonine diastereomers (2S,3S)-(-)-2-amino-3,4-dihydroxybutyric acid and (2R,3S)-(+)-2-amino-3,4-dihydroxybutyric acid, respectively. For a synthesis of the enantiomer of the latter compound, see: Pirrung, M. C.; Nunn, D. S.; McPhail, A. T.; Mitchell, R. E. Bioorg. Med. Chem. Lett. 1993, 3, 2095-2098. For the definitive configurational assignments of β-hydroxythreonine stereoisomers, see: Hamel, E. E.; Painter, E. P. J. Am. Chem. Soc. 1953, 75, 1362-1368. Niemann, C.; Nichols, P. L. J Biol. Chem. 1942, 143, 191-199.
29. Derdau, V.; Snieckus, V. J. Org. Chem. 2001, 66, 1992-1998.
30. Kim, B. J.; Park, Y. S.; Beak, P. J. Org. Chem. 1999, 64, 1705-1708 and references cited within. For a review of enantioselective deprotonations using chiral bases, see: O'Brien, P. J. Chem. Soc., Perkin Trans. 1998, 1439.
31. Kim, B. J.; Park, Y. S.; Beak, P. J. Org. Chem. 1999, 64, 1705-1708 and references cited within. For a review of enantioselective deprotonations using chiral bases, see: O'Brien, P. J. Chem. Soc., Perkin Trans. 1998, 1439.
32. 4-promoted aldol reactions of chiral N-acyloxazolidinethiones has been reported (Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894-902). In view of the fact that similar, very high diastereoselectivities were obtained under these highly coordinating conditions, even when achiral tert-amines were substituted for (-)-sparteine, the role of the chiral diamine in enantiodifferentiation is somewhat masked.
33. 4-promoted aldol reactions of chiral N-acyloxazolidinethiones has been reported (Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894-902). In view of the fact that similar, very high diastereoselectivities were obtained under these highly coordinating conditions, even when achiral tert-amines were substituted for (-)-sparteine, the role of the chiral diamine in enantiodifferentiation is somewhat masked.
34. For enantioselective additions of aggregates of organolithiums/chiral aminoalkoxides to aldehydes and ketones, see: Briggs, T. F.; Winemiller, M. D.; Xiang, B.; Collum, D. B. J. Org. Chem. 2001, 66(19), 6291-6298 and references cited within.
35. Since the aldol reaction mixtures were observed to be heterogeneous and contained sparingly soluble white precipitates, we cannot discount the possibility that reactions occur at the surface of heterogeneous chiral aggregates which influence the stereochemical outcome.
36. Normal phase HPLC(10 × 250 mm, 0.5% i-PrOH:hexane, 2.0 mL/ min).
37. For an alternate five-step synthesis of (S)-N-BOC-β-aminodecanoic acid from nonanoyl chloride, see: Expósito, A.; Fernández-Suárez, M.; Iglesias, T.; Muñoz, L.; Riguera, R. J. Org. Chem. 2001, 66, 4206-4213.
38. 3CN:50 mM triethylammonium phosphate, aq, 1.0 mL/min). To obtain the retention times of ent-2a,2b and ent-3a,3b the amino acids 2a,2b and 3a,3b were reacted with the "ent-" Marfey's reagent [(2,4-dinitro-5-fluorophenylamino)-D-alaninamide], prepared from D-alaninamide according to Marfey. L-Valine and D-glutamine (as D-glutamate) were determined separately using chiral HPLC (D-penicillamine-based column).
39. Gerwick, W. H.; Jiang, Z. D.; Agarwal, S. K.; Farmer, B. T. Tetrahedron 1992, 48, 2313-2324.
40. (a) Bonnard, I.; Rolland, M.; Francisco, C.; Benaigs, B. Lett. Pept. Sci. 1997, 4, 289-292.
41. (b) Frankmölle, W. P.; Larsen, L. K.; Caplan, F. R.; Patterson, G. M. L.; Knübel, G.; Levine, I. A.; Moore, R. E. J. Antibiot. 1992, 45, 1451-1457.
42. The remainder of the amino acid residues in 1 were determined by Marfey's procedure as L-Ala, N-Me-L-Ile, allo-L-Thr (×2), and trans-L-Hpro using commercially available standards.