Total synthesis of mycestericin A and its 14-epimer

Tetrahedron

Volumn 65, Issue 45, 2009, Pages 9188-9201

  Yamanaka, Hiroyoshi ^a   Sato, Kazuya ^a   Sato, Hideyuki ^a   Iida, Masatoshi ^a   Oishi, Takeshi ^a   Chida, Noritaka ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Mycestericin A; Negishi coupling; Overman rearrangement; Suzuki Miyaura coupling; Total synthesis

Indexed keywords

1 [OXIRAN 2 YL]HEPTAN 1 OL; 2 [(4 [(TERT BUTYLDIPHENYLSILYLOXY)METHYL] 2,2 DIMETHYL 1,3 DIOXAN 5 YLIDENE)ETHANOL; 2 [1 (METHOXYMETHOXY)HEPTYL]OXIRANE; 2 [1 [(2 (TRIMETHYLSILYL)ETHOXY)METHOXY]HEPTYL]OXIRANE; 2,2 DIMETHYL 5 HEXYL 1,3 DIOXOLAN 4 YL]METHANOL 4 METHYLBENZENESULFONATE; 4 (METHOXYMETHOXY)DEC 2 EN 1 OL; 4 [(TERT BUTYLDIPHENYLSILYLOXY)METHYL] 2,2 DIMETHYL 1,3 DIOXAN 5 OL; 4 [[(TRIMETHYLSILYL)METHOXY]ETHOXY]DEX 2 EN 1 OL; 4 ACETAMIDO 4 (ACETOXYMETHYL) 2 [3 IODOALLYL] 5 OXOTETRAHYDROFURAN 3 YL ACETATE; 4 ACETAMIDO 4 (ACETOXYMETHYL) 2 ALLYL 5 OXOTETRAHYDROFURAN 3 YL ACETATE; [[(4S,5S) 5 (BENZYLOXY) 2,2 DIEMTHYL 1,3 DIOXAN 4 YL]METHOXY] (TERT BUTYL) DIPHENYLSILANE; ALLYL COMPOUND; CARBON; ETHYL 2 [4 [(TERT BUTYLDIPHENYLSILYLOXY)METHYL] 2,2 DIMETHYL 1,3 DIOXAN 5 YLIDENE]ACETATE; GAMMA LACTONE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; IODIDE; METAL; METHYL 2,2 DIMETHYL 4 (HYDROXYMETHYL) 5 (2,2,2 TRICHLOROACETAMIDO) 1,3 DIOXANE 5 CARBOXYLATE; METHYL 2,2 DIMETHYL 4 [ 4 IODO 1 (METHOXYMETHOXY0BUT 3 ENYL] 5 (2,2,2 TRICHLOROACETAMIDO) 1,3 DIOXANE 5 CARBOXYLATE; METHYL 2,2 DIMETHYL 4 [1 9METHOXYMETHOXY)BUT 3 ENYL] 5 (2,2,2 TRICHLOROACETAMIDO) 1,3 DIOXANE 5 CARBOXYLATE; METHYL 2,2 DIMETHYL 4 [1 HYDROXYBUT 3 ENYL] 5 (2,2,2 TRICHLOROACETAMIDO) 1,3 DIOXANE 5 CARBOXYLATE; METHYL 4 [(TERT BUTYLDIPHENYLSILYLOXY)MEHTYL] 2,2 DIEMETHYL 5 (2,2,2 TRICHLOROACETAMIDO) 1,3 DIOXANNE 5 CARBOXYLATE; MYCESTERICIN A; N [4 [(TERT BUTYLDIPHENYLSILYLOXY)METHYL] 2,2 DIMETHYL 5 VINYL 1,3 DIOXAN 5 YL] 2,2,2 TRICHLOROACETAMIDE; NITROGEN; TARTARIC ACID; TERT BUTYL[(1 [OXYRAN 2 YL]HEPTYLOXY]DIPHENYLSILANE; TRICHLOROACETIMIDIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CROSS COUPLING REACTION; DEPROTECTION REACTION; DRUG DEGRADATION; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMER; HYDROPHOBICITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SUZUKI REACTION;

TETRA;

EID: 70349761376     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.012     Document Type: Article

References (96)

1. Sasaki S., Hashimoto R., Kiuchi M., Inoue K., Ikumoto T., Hirose R., Chiba K., Hoshino Y., Okumoto T., and Fujita T. J. Antibiot. 47 (1994) 420-433
2. Fujita T., Hamamichi N., Kiuchi M., Matsuzaki T., Kitao Y., Inoue K., Hirose R., Yoneta M., Sasaki S., and Chiba K. J. Antibiot. 49 (1996) 846-853
3. Klurpfel D., Bagli J., Baker H., Charest M.-P., Kudelski A., Sehgal S.N., and Vézina C. J. Antibiot. 25 (1972) 109-115
4. Bagli J.F., Kluepfel D., and Jacques M.S. J.Org. Chem. 38 (1973) 1253-1260
5. Aragozzini F., Manachini P.L., Craveri R., Rindone B., and Scolastico C. Tetrahedron 28 (1972) 5493-5498
6. Fujita T., Inoue K., Yamamoto S., Sasaki S., Toyama R., Yoneta M., Hoshino Y., and Okumoto T. J. Antibiot. 47 (1994) 208-215
7. Fujita T., Inoue K., Yamamoto S., Ikumoto T., Sasaki S., Toyama R., Yoneta M., Chiba K., Hoshino Y., and Okumoto T. J. Antibiot. 47 (1994) 216-225
8. Sasaki S., Hashimoto R., Kiuchi M., Inoue K., Ikumoto T., Hirose R., Chiba K., Hoshino Y., Okumoto T., and Fujita T. J. Antibiot. 47 (1994) 420-433
9. Brunner M., and Koskinen A.M.P. Curr. Org. Chem. 8 (2004) 1629-1645
10. For isolation of sphingofungins A-D, see:
11. VanMiddlesworth F., Giacobbe R.A., Lopez M., Garrity G., Bland J.A., Batizal K., Frontling R.A., Wilson K.E., and Monaghan R.L. J. Antibiot. 45 (1992) 861-867
12. VanMiddlesworth F., Dufresne C., Wincott F.E., Mosley R.T., and Wilson K.E. Tetrahedron Lett. 33 (1992) 297-300 For isolation of sphingofungins E and F, see:
13. Horn W.S., Smith J.L., Bills G.F., Raghoobar S.L., Helms G.L., Kurta M.B., Marrinan J.A., Frommer B.R., Thornton R.A., and Mandala S.M. J. Antibiot. 45 (1992) 1692-1696
14. Yamaji-Hasegawa A., Takahashi A., Tetsuka Y., Senoh Y., and Kobayashi T. Biochemistry 44 (2005) 268-277
15. Miyake Y., Kozutumi Y., Nakamura S., Fujita T., and Kawasaki T. Biochem. Biophys. Res. Commun. 211 (1995) 396-403
16. Zweerink M.M., Edison A.M., Wells G.B., Pinto W., and Lester R.L. J. Biol. Chem. 267 (1992) 25032-25038
17. Recent reviews of synthesis of natural products possessing α-substituted α-amino acid structures, see:
18. Kang S.H., Kang S.Y., Lee H.-S., and Buglass A.J. Chem. Rev. 105 (2005) 4537-4558
19. Ohfune Y., and Shinada T. Eur. J. Org. Chem. (2005) 5127-5143
20. Cativiela C., and Díaz-de-Villegas M.D. Tetrahedron: Asymmetry 18 (2007) 569-623
21. Recent reviews on chemistry and biological activities of myriocin-related compounds, see:
22. Byun H.-S., Lu X., and Bittman R. Synthesis (2006) 2447-2474
23. Liao J., Tao J., Lin G., and Liu D. Tetrahedron 61 (2005) 4715-4733
24. For total synthesis of myriocin, see:
25. Banfi L., Beretta M.G., Colombo L., Gennari C., and Scolastico C. J. Chem. Soc., Chem. Commun. (1982) 488-490
26. J. Chem. Soc., Perkin Trans. 1 (1983) 1613-1619
27. Yoshikawa M., Yokokawa Y., Okuno Y., and Murakami N. Chem. Pharm. Bull. 42 (1994) 994-996
28. Tetrahedron 51 (1995) 6209-6228
29. Sano S., Kobayashi Y., Kondo T., Takebayashi M., Maruyama S., Fujita T., and Nagao Y. Tetrahedron Lett. 36 (1995) 2097-2100
30. Hatakeyama S., Yoshida M., Esumi T., Iwabuchi Y., Irie H., Kawamoto T., Yamada H., and Nishizawa M. Tetrahedron Lett. 38 (1997) 7887-7890
31. Oishi T., Ando K., and Chida N. Chem. Commun. (2001) 1932-1933
32. Lee K.-Y., Oh C.-Y., Kim Y.-H., Joo J.-E., and Ham W.-H. Tetrahedron Lett. 43 (2002) 9361-9363
33. Martinková M., Gonda J., Raschmanová J., and Vojticková M. Tetrahedron 63 (2007) 10603-10607
34. Jones M.C., and Marsden S.P. Org. Lett. 10 (2008) 4125-4128
35. Inai M., Toto T., Furuta T., Wakimoto T., and Kan T. Tetrahedron: Asymmetry 19 (2008) 2771-2773
36. For total synthesis of sphingofungins E and/or F, see:
37. Kobayashi S., Matsumura M., Furuta T., Hayashi T., and Iwamoto S. Synlett (1997) 301-303
38. Kobayashi S., Furuta T., Hayashi T., Nishijima M., and Hanada K. J. Am. Chem. Soc. 120 (1998) 908-919
39. Kobayashi S., and Furuta T. Tetrahedron 54 (1998) 10275-10294
40. Trost B.M., and Lee C.B. J. Am. Chem. Soc. 120 (1998) 6818-6819
41. Trost B.M., and Lee C. J. Am. Chem. Soc. 123 (2001) 12191-12201
42. Liu D.-G., Wang B., and Lin G.-Q. J. Org. Chem. 65 (2000) 9114-9119
43. Wang B., Yu X.-M., and Lin G.-Q. Synlett (2001) 904-906
44. Nakamura T., and Shiozaki M. Tetrahedron Lett. 42 (2001) 2701-2704
45. Tetrahedron 58 (2002) 8779-8791
46. Oishi T., Ando K., Inomiya K., Sato H., Iida M., and Chida N. Org. Lett. 4 (2002) 151-154
47. Bull. Chem. Soc. Jpn. 75 (2002) 1927-1947
48. Lee K.-Y., Oh C.-Y., and Ham W.-H. Org. Lett. 4 (2002) 4403-4405
49. Li M., and Wu A. Synlett (2006) 2985-2988
50. For total synthesis of mycestericins, see:
51. Fujita T., Hamamichi N., Matsuzaki T., Kitao Y., Kiuchi M., Node M., and Hirose R. Tetrahedron Lett. 36 (1995) 8599-8602
52. Shibata K., Shingu K., Vassilev V.P., Nishide K., Fujita T., Node M., Kajimoto T., and Wong C.-H. Tetrahedron Lett. 37 (1996) 2791-2794
53. Nishide K., Shibata K., Fujita T., Kajimoto T., Wong C.-H., and Node M. Heterocycles 52 (2000) 1191-1201
54. Iwabuchi Y., Furukawa M., Esumi T., and Hatakeyama S. Chem. Commun. (2001) 2030-2031 Synthesis and biological activity of sulfamisterin and its derivatives, see:
55. Sato H., Maeba T., Yanase R., Yamaji-Hasegawa A., Kobayashi T., and Chida N. J. Antibiot. 58 (2005) 37-49
56. A part of this work has been published as a preliminary communication, see:. Sato H., Sato K., Iida M., Yamanaka H., Oishi T., and Chida N. Tetrahedron Lett. 49 (2008) 1943-1947
57. Chida N., Takeoka J., Tsutsumi N., and Ogawa S. J. Chem. Soc., Chem. Commun. (1995) 793-794
58. Chida N., Takeoka J., Ando K., Tsutsumi N., and Ogawa S. Tetrahedron 53 (1997) 16287-16298
59. For a comprehensive review on Overman rearrangement and related reactions, see:. Overman L.E., and Carpenter N.E. In: Overman L.E. (Ed). Organic Reactions Vol. 66 (2005), Wiley, New York, NY 1-107
60. Recent reports on syntheses of natural products and related compounds utilizing Overman rearrangement, see:
61. Momose T., Kaiya Y., Hasegawa J., Sato T., and Chida N. Synthesis (2009) 2983-2991
62. Imaoka T., Iwamoto O., Noguchi K., and Nagasawa K. Angew. Chem., Int. Ed. 48 (2009) 3799-3801
63. Hama N., Matsuda T., Sato T., and Chida N. Org. Lett. 11 (2009) 2687-2690
64. Dickson D.P., and Wardrop D.J. Org. Lett. 11 (2009) 1341-1344
65. Momose T., Hama N., Higashino C., Sato H., and Chida N. Tetrahedron Lett. 49 (2008) 1376-1379
66. Matveenko M., Kokas O.J., Banwell M.G., and Willis A.C. Org. Lett. 9 (2007) 3683-3685
67. Hakansson A.E., Palmelund A., Holm H., and Madsen R. Chem.-Eur. J. 12 (2006) 3243-3253
68. Tsujimoto T., Nishikawa T., Urabe D., and Isobe M. Synlett (2005) 433-436
69. Nishikawa T., Urabe D., Yoshida K., Iwabuchi T., Asai M., and Isobe M. Chem.-Eur. J. 10 (2004) 452-462
70. Ohyabu N., Nishikawa T., and Isobe M. J. Am. Chem. Soc. 125 (2003) 8798-8805
71. Sánchez-Sancho F., Valverde S., and Herradón B. Tetrahedron: Asymmetry 7 (1996) 3209-3246
72. Nishikawa T., Asai M., Ohyabu N., and Isobe M. J. Org. Chem. 63 (1998) 188-192
73. The optical purities of 14, 5a, and 5b were all determined to be >99% ee, by chiral column analyses (Chiralcel OD-H), confirming that no racemization had occurred during the preparation of these compounds. See Experimental section.
74. Keck G.E., and Boden E.P. Tetrahedron Lett. 25 (1984) 265-268
75. Marshall J.A. Chem. Rev. 100 (2000) 3163-3186
76. Ohba S., Sato H., Iida M., and Chida N. Acta Crystallogr., Sect. E E59 (2003) o1259-o1260
77. Takai K., Nitta K., and Utimoto K. J. Am. Chem. Soc. 108 (1986) 7408-7410
78. Evans D.A., and Black W.C. J. Am. Chem. Soc. 115 (1993) 4497-4513
79. Carmack M., and Kelly C.J. J. Org. Chem. 33 (1968) 2171-2173
80. Rubin L.J., Lardy H.A., and Fischer H.O.L. J. Am. Chem. Soc. 74 (1952) 425-428
81. Narisada M., Ohtami M., Watanabe F., Uchida K., Arita H., Doteuchi M., Hanasaki K., Kakushi H., Otani K., and Hara S. J. Med. Chem. 31 (1988) 1847-1854
82. Taber D.F., Deker P.B., and Gaul M.D. J. Am. Chem. Soc. 109 (1987) 7488-7494
83. Negishi E. Pure Appl. Chem. 53 (1981) 2333-2356
84. Negishi E. Acc. Chem. Res. 15 (1982) 340-348
85. Williams D.R., and Kissel W.S. J. Am. Chem. Soc. 120 (1998) 11198-11199
86. Tamaru Y., Ochiai H., Nakamura T., and Yoshida Z. Angew. Chem., Int. Ed. Engl. 26 (1987) 1157-1158
87. Negishi E. Bull. Chem. Soc. Jpn. 80 (2007) 233-257
88. The structure of 25 has been tentatively assigned; there is a possibility that compound 25 would be a positional isomer of the conjugated carbon-carbon double bonds.
89. Isobe M., Ichikawa Y., Bai D.-L., Masaki H., and Goto T. Tetrahedron 43 (1987) 4767-4776
90. 4NF in THF or CsF in HMPA
91. The low yield of this step was mainly due to the decomposition of the substrate; the formation of polar by-products, whose structures could not be determined, was observed.
92. For a review on the Suzuki-Miyaura coupling, see:
93. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457-2483 For a review on the B-alkyl Suzuki-Miyaura coupling, see:
94. Chemler S.R., Trauner D., and Danishefsky S.J. Angew. Chem., Int. Ed. 40 (2001) 4544-4568
95. Johnson C.R., and Braun M.P. J. Am. Chem. Soc. 115 (1993) 11014-11015
96. The optical purities of 23c and ent-23c were determined to be >99% ee, by chiral column analyses (Chiralcel OD-H) of the derived alcohols 24c and ent-24c. See Experimental section.