General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form

Journal of Organic Chemistry

Volumn 79, Issue 5, 2014, Pages 2226-2241

  Chung, Won Jin ^a   Carlson, Joseph S ^a   Vanderwal, Christopher D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS METATHESIS; EPOXIDE INTERMEDIATE; KINETIC RESOLUTION; SECOND-GENERATION SYNTHESIS;

CHEMISTRY;

ORGANIC COMPOUNDS;

DANICALIPIN A; LIPID; MALHAMENSILIPIN A; MYTILIPIN A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; SYNTHESIS;

KINETICS; LIPIDS; MOLECULAR STRUCTURE; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 84896744848     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5000829     Document Type: Article

References (80)

1. Bedke, D. K.; Vanderwal, C. D. Nat. Prod. Rep. 2011, 28, 15-25
2. Nilewski, C.; Carreira, E. M. Eur. J. Org. Chem. 2012, 1685-1698
3. Elovson, J.; Vagelos, P. R. Proc. Natl. Acad. Sci. U.S.A. 1969, 62, 957-963
4. Haines, T. H.; Pousada, M.; Stern, B.; Mayers, G. L. Biochem. J. 1969, 113, 565-566
5. Mayers, G. L.; Pousada, M.; Haines, T. H. Biochemistry 1969, 8, 2981-2986
6. Elovson, J.; Vagelos, P. R. Biochemistry 1970, 9, 3110-3126
7. Haines, T. H. Prog. Chem. Fats Lipids 1971, 11, 297-345
8. Haines, T. H. Annu. Rev. Microbiol. 1973, 27, 403-412
9. Chen, J. L.; Proteau, P. J.; Roberts, M. A.; Gerwick, W. H.; Slate, D. L.; Lee, R. H. J. Nat. Prod. 1994, 57, 524-527
10. Ciminiello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Di Rosa, M.; Ianaro, A.; Poletti, R. J. Org. Chem. 2001, 66, 578-582
11. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Forino, M.; Di Rosa, M.; Ianaro, A.; Poletti, R. J. Am. Chem. Soc. 2002, 124, 13114-13120
12. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Forino, M.; Magno, S.; Di Meglio, P.; Ianaro, A.; Poletti, R. Tetrahedron 2004, 60, 7093-7098
13. Kawahara, T.; Kumaki, Y.; Kamada, T.; Ishii, T.; Okino, T. J. Org. Chem. 2009, 74, 6016-6024
14. Chao, C.-H.; Huang, H.-C.; Wang, G.-H.; Wen, Z.-H.; Wang, W.-H.; Chen, I.-M.; Sheu, J.-H. Chem. Pharm. Bull. 2010, 58, 944-946
15. Nilewski, C.; Geisser, R. W.; Carreira, E. M. Nature 2009, 457, 573-576
16. Nilewski, C.; Geisser, R. W.; Ebert, M.-O.; Carreira, E. M. J. Am. Chem. Soc. 2009, 131, 15866-15876
17. Nilewski, C.; Deprez, N. R.; Fessard, T. C.; Li, D. B.; Geisser, R. W.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 7940-7943
18. Geisser, R. W. D.Sc Dissertation, ETH Zürich, 2010.
19. Yoshimitsu, T.; Fujumoto, N.; Tanaka, T. J. Org. Chem. 2009, 74, 696-702
20. Yoshimitsu, T.; Fujumoto, N.; Nakatani, R.; Kojima, N.; Tanaka, T. J. Org. Chem. 2010, 75, 5425-5437
21. Yoshimitsu, T.; Nakatani, R.; Kobayashi, A.; Tanaka, T. Org. Lett. 2011, 13, 908-911
22. Umezawa, T.; Shibata, M.; Kaneko, K.; Okino, T.; Matsuda, F. Org. Lett. 2011, 13, 904-907
23. Shibuya, G.; Kanady, J.; Vanderwal, C. D. J. Am. Chem. Soc. 2008, 130, 12514-12518
24. Bedke, D. K.; Shibuya, G. M.; Pereira, A.; Gerwick, W. H.; Haines, T. H.; Vanderwal, C. D. J. Am. Chem. Soc. 2009, 131, 7570-7572
25. Pereira, A. R.; Byrum, T.; Shibuya, G. M.; Vanderwal, C. D.; Gerwick, W. H. J. Nat. Prod. 2010, 73, 279-283
26. Bedke, D. K.; Shibuya, G. M.; Pereira, A.; Gerwick, W. H.; Vanderwal, C. D. J. Am. Chem. Soc. 2010, 132, 2542-2543
27. Chung, W.-j.; Carlson, J. S.; Bedke, D. K.; Vanderwal, C. D. Angew. Chem., Int. Ed. 2013, 52, 10052-10055
28. Chung, W.-j.; Vanderwal, C. D. Acc. Chem. Res. 2014, DOI: 10.1021/ar400246w.
29. Carbonyl additions to simple α-chloroaldehydes are often highly diastereoselective. See: Britton, R.; Kang, B. Nat. Prod. Rep. 2013, 30, 227-236
30. The addition of organometallic nucleophiles to α-chloroaldehydes generally proceeds to afford the anti product, consistent with the polar Felkin-Anh model (hyperconjugative stabilization of the transition state/steric control), though the Cornforth model (dipole minimization/steric control) also accounts for the stereochemistry of the products. For an excellent discussion and lead reference, see: Cee, V. J.; Cramer, C. J.; Evans, D. A. J. Am. Chem. Soc. 2006, 128, 2920-2930
31. The corresponding chloroallylaluminum reagents have been previously reported: Hosomi, A.; Kohra, S.; Tominaga, Y.; Ando, M.; Sakurai, H. Chem. Pharm. Bull. 1987, 35, 3058-3061
32. Hu, S.; Jayaraman, S.; Oehlschlager, A. C. J. Org. Chem. 1996, 61, 7513-7520
33. Hu, S.; Jayaraman, S.; Oehlschlager, A. C. J. Org. Chem. 1998, 63, 8843-8849
34. Nicolaou, K. C.; Simmons, N. L.; Ying, Y.; Heretsch, P. M.; Chen, J. S. J. Am. Chem. Soc. 2011, 133, 8134-8137
35. Hu, D. X.; Shibuya, G. M.; Burns, N. Z. J. Am. Chem. Soc. 2013, 135, 12960-12963
36. Halpern, O. S. M.S. Dissertation, UC Irvine, 2008.
37. Schlama, T.; Gabriel, K.; Gouverneur, V.; Mioskowski, C. Angew. Chem., Int. Ed. 1997, 36, 2341-2344
38. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496-6502
39. Nordin, O.; Nguyen, B.-V.; Vörde, C.; Hedenström, E.; Högberg, H.-E. J. Chem. Soc., Perkin Trans. 1 2000, 367-376 and references therein
40. Ghanem, A.; Aboul-Enein, H. Y. Chirality 2004, 17, 1-15
41. Kobayashi, S.; Endo, T.; Ueno, M. Angew. Chem., Int. Ed. 2011, 50, 12262-12265
42. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240
43. Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L.; Fiaud, J. C., Eds.; Wiley: New York, 1988; Vol. 18, pp 249-330.
44. Hoveyda, A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 537-574
45. Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885
46. Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26
47. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974-4001
48. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687-2688
49. Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 1374-1377
50. White, D. E.; Jacobsen, E. N. Tetrahedron: Asymmetry 2003, 14, 3633-3638
51. Birrell, J. A.; Jacobsen, E. N. Org. Lett. 2013, 15, 2895-2897
52. Denmark, S. E.; Barsanti, P. A.; Wong, K.-T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428-2429
53. Denmark, S. E.; Barsanti, P. A.; Beutner, G. L.; Wilson, T. W. Adv. Synth. Catal. 2007, 349, 567-582
54. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560-1638
55. Tarasevych, A. V.; Sorochinsky, A. E.; Kukhar, V. P.; Guillemin, J.-C. Origins Life Evol. Biospheres 2013, 43, 129-135 and references therein
56. For the first application of Z -selective alkene cross metathesis in natural product synthesis, see: Meek, S. J.; O'Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature 2011, 471, 461-466
57. Leggans, E. K.; Barker, T. J.; Duncan, K. K.; Boger, D. L. Org. Lett. 2012, 14, 1428-1431
58. Endo, K.; Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, 8525-8527
59. Keitz, B. K.; Endo, K.; Herbert, M. B.; Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, 9686-9688
60. Keitz, B. K.; Endo, K.; Patel, P. R.; Herbert, M. B.; Grubbs, R. H. J. Am. Chem. Soc. 2012, 134, 693-699
61. Liu, P.; Xu, X.; Dong, X.; Keitz, B. K.; Herbert, M. B.; Grubbs, R. H.; Houk, K. N. J. Am. Chem. Soc. 2012, 134, 1464-1467
62. Keitz, B. K.; Fedorov, A.; Grubbs, R. H. J. Am. Chem. Soc. 2012, 134, 2040-2043
63. Herbert, M. B.; Lan, Y.; Keitz, B. K.; Liu, P.; Endo, K.; Day, M. W.; Houk, K. N.; Grubbs, R. H. J. Am. Chem. Soc. 2012, 134, 7861-7866
64. Herbert, M. B.; Marx, V. M.; Pederson, R. L.; Grubbs, R. H. Angew. Chem., Int. Ed. 2013, 52, 310-314
65. Marx, V. M.; Herbert, M. B.; Keitz, B. K.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 94-97
66. Rosebrugh, L. E.; Herbert, M. B.; Marx, V. M.; Keitz, B. K.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 1276-1279
67. Miyazaki, H.; Herbert, M. B.; Liu, P.; Dong, X.; Xu, X.; Keitz, B. K.; Ung, T.; Mkrtumyan, G.; Houk, K. N.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 5848-5858
68. Cannon, J. S.; Grubbs, R. H. Angew. Chem., Int. Ed. 2013, 52, 9001-9004
69. Rosebrugh, L. E.; Marx, V. M.; Keitz, B. K.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 10032-10035
70. Hartung, J.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 10183-10185
71. Endo, K.; Herbert, M. B.; Grubbs, R. H. Organometallics 2013, 32, 5128-5135
72. Quigley, B. L.; Grubbs, R. H. Chem. Sci. 2014, 5, 501-506
73. Odinokov, V. N.; Ishmuratov, G. Y.; Vakhidov, R. R.; Berg, A. A.; Muslukhov, R. R.; Tolstikov, G. A. Chem. Nat. Compd. 1992, 28, 237-240
74. Samojłowicz, C.; Bieniek, M.; Zarecki, A.; Kadyrovb, R.; Grela, K. Chem. Commun. 2008, 44, 6282-6284
75. Hong, S. H.; Sander, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160-17161
76. Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136
77. Wdowik, T.; Samojłowicz, C.; Jawiczuk, M.; Malińska, M.; Woźniakb, K.; Grela, K. Chem. Commun. 2013, 49, 674-676
78. Kotani, S.; Hashimoto, S.; Nakajima, M. Tetrahedron 2007, 63, 3122-3132
79. Cabezas, J. A.; Oehlschlager, A. C. Synthesis 1999, 1, 107-111
80. Odinokov, V. N.; Ishmuratov, G. Yu.; Vakhidov, R. R.; Berg, A. A.; Muslukhov, R. R.; Tolstikov, G. A. Chem. Nat. Compd. 1992, 28, 237-240