Two-phase terpene total synthesis: Historical perspective and application to the Taxol® problem

Synlett

Volumn , Issue 12, 2010, Pages 1733-1745

  Ishihara, Yoshihiro ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

biomimetic synthesis; oxidation; pyramid; terpenoids; total synthesis

Indexed keywords

4 EPI AJANOL; CARBON; DIHYDROXYEUDESMANE; EUDESMANE DERIVATIVE; EUDESMANE DIHYDROJENENOL; HYDROGEN; PACLITAXEL; TERPENE; UNCLASSIFIED DRUG;

BIOCATALYST; BIOCHEMISTRY; BIOMIMETICS; CHEMICAL BINDING; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; HYDROXYLATION; REVIEW;

EID: 77954842094     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258123     Document Type: Review

References (125)

1. Some reviews on CH activation include: (a) Stahl S S., Labinger J A., Bercaw J E., Angew. Chem. Int. Ed. 1998 37 2180
2. (b) Crabtree R H., J. Chem. Soc., Dalton Trans. 2001 2437
3. (c) Godula K, Sames D, Science 2006 312 67
4. (d) Davies H M. L., Manning J R., Nature 2008 451 417
5. (e) Giri R, Shi B.-F, Engle K M., Maugel N, Yu J.-Q, Chem. Soc. Rev. 2009 38 3242
6. Representative examples include: (a) Barton D H. R., Beaton J M., Geller L E., Pechet M M., J. Am. Chem. Soc. 1960 82 2640
7. (b) Barton D H. R., Beaton J M., J. Am. Chem. Soc. 1960 82 2641
8. (c) Barton D H. R., Beaton J M., Geller L E., Pechet M M., J. Am. Chem. Soc. 1961 83 4076
9. (d) Akhtar M, Barton D H. R., J. Am. Chem. Soc. 1964 86 1528
10. Representative examples include: (a) Breslow R, Baldwin S W., J. Am. Chem. Soc. 1970 92 732
11. (b) Breslow R, Scholl P C., J. Am. Chem. Soc. 1971 93 2331
12. (c) Breslow R, Baldwin S, Flechtner T, Kalicky P, Liu S, Washburn W, J. Am. Chem. Soc. 1973 95 3251
13. (d) Breslow R, Corcoran R J., Snider B B., Doll R J., Khanna P L., Kaleya R, J. Am. Chem. Soc. 1977 99 905
14. Breslow R, Yang J, Yan J, Tetrahedron 2002 58 653
15. Shenvi R A., OMalley D P., Baran P S., Acc. Chem. Res. 2009 42 530
16. Baran P S., Maimone T J., Richter J M., Nature 2007 446 404
17. Young I S., Baran P S., Nature Chem. 2009 1 193
18. Burns N Z., Baran P S., Hoffmann R W., Angew. Chem. Int. Ed. 2009 48 2854
19. Newhouse T, Baran P S., Hoffmann R W., Chem. Soc. Rev. 2009 38 3010
20. Gaich T, Baran P S., J. Org. Chem. 2010 DOI: 10.1021/jo1006812
21. Maimone T J., Baran P S., Nat. Chem. Biol. 2007 3 396
22. This classic reaction is present in numerous undergraduate and graduate organic textbooks for example:, Smith M B., March J, Marchs Advanced Organic Chemistry: Reactions Mechanisms and Structure John Wiley & Sons New York 2001 894-969
23. (a) Hofmann A W., Ber. 1885 18 109
24. (b) Löffler K, Freytag C, Ber. 1909 42 3427
25. (a) Wawzonek S, Thelen P J., J. Am. Chem. Soc. 1950 72 2118
26. (b) Wawzonek S, Nelson M F., Thelen P J., J. Am. Chem. Soc. 1951 73 2806
27. (c) Buchschacher P, Kalvoda J, Arigoni D, Jeger O, J. Am. Chem. Soc. 1958 80 2905
28. (d) Wawzonek S, Culbertson T P., J. Am. Chem. Soc. 1959 81 3367
29. Corey E J., White R W., J. Am. Chem. Soc. 1958 80 6686
30. Cainelli G, Mihailovic M Lj, Arigoni D, Jeger O, Helv. Chim. Acta 1959 42 1124
31. Breslow R, Chem. Soc. Rev. 1972 1 553
32. Breslow R, Acc. Chem. Res. 1980 13 170
33. Representative examples include
34. (a) Barton D H. R., Gastiger M J., Motherwell W B., J. Chem. Soc., Chem. Commun. 1983 41
35. (b) Barton D H. R., Bévière S D., Doller D, Tetrahedron Lett. 1991 32 4671
36. (c) Barton D H. R., Bévière S D., Chavasiri W, Csuhai E, Doller D, Liu W G., J. Am. Chem. Soc. 1992 114 2147
37. (d) Barton D H. R., Doller D, Acc. Chem. Res. 1992 25 504
38. Representative examples include: (a) Breslow R, Huang Y, Zhang X, Yang J, Proc. Nat. Acad. Sci. 1997 94 11156
39. (b) Breslow R, Zhang X, Huang Y, J. Am. Chem. Soc. 1997 119 4535
40. (c) Fang Z, Breslow R, Org. Lett. 2006 8 251
41. (a) Sarneski J E., Michos D, HoldenThorp H, Didiuk M, Poon T, Blewitt J, Brudvig G W., Crabtree R H., Tetrahedron Lett. 1991 32 1153
42. (b) Wessel J, Crabtree R H., J. Mol. Catal. A: Chem. 1996 113 13
43. (c) Chen K, Que L Jr., J. Am. Chem. Soc. 2001 123 6327
44. (d) Chen M S., White M C., Science 2007 318 783
45. (e) Barluenga J, Gonzlez-Bobes F, Gonzlez J M., Angew. Chem. Int. Ed. 2002 41 2556
46. (f) Crabtree R H., Mihelcic J M., Quirk J M., J. Am. Chem. Soc. 1979 101 7738
47. (g) Tenaglia A, Terranova E, Waegell B, Tetrahedron Lett. 1989 30 5271
48. (h) Murray R W., Iyanar K, Chen J, Wearing J T., Tetrahedron Lett. 1995 36 6415
49. (i) Lee S, Fuchs P L., J. Am. Chem. Soc. 2002 124 13978
50. (j) Kamata K, Yonehara K, Nakagawa Y, Uehara K, Mizuno N, Nature Chem. 2010 2 478
51. (k) Mello R, Fiorentino M, Fusco C, Curci R, J. Am. Chem. Soc. 1989 111 6749
52. (l) DesMarteau D D., Donadelli A, Montanari V, Petrov V A., Resnati G, J. Am. Chem. Soc. 1993 115 4897
53. (m) Brodsky B H., DuBois J, J. Am. Chem. Soc. 2005 127 15391
54. (n) Moody C J., OConnell J L., Chem. Commun. 2000 1311
55. (o) Kaufman M D., Grieco P A., Bougie D W., J. Am. Chem. Soc. 1993 115 11648
56. (p) Concepcin J I., Francisco C G., Hernndez R, Salazar J A., Surez E, Tetrahedron Lett. 1984 25 1953
57. (q) Chen K, Richter J M., Baran P S., J. Am. Chem. Soc. 2008 130 7247
58. (r) Carr K, Sutherland J K., J. Chem. Soc., Chem. Commun. 1984 1227
59. (s) Baldwin J E., Jones R H., Najera C, Yus M, Tetrahedron 1985 41 699
60. (t) Kao L.-C, Sen A, J. Chem. Soc., Chem. Commun. 1991 1242
61. (u) Dangel B D., Johnson J A., Sames D, J. Am. Chem. Soc. 2001 123 8149
62. (v) Desai L V., Hull K L., Sanford M S., J. Am. Chem. Soc. 2004 126 9542
63. (w) Giri R, Liang J, Lei J.-G, Li J.-J, Wang D.-H, Chen X, Naggar I C., Guo C, Foxman B M., Yu J.-Q, Angew. Chem. Int. Ed. 2005 44 7420
64. (x) Wong M.-K, Chung N.-W, He L, Wang X.-C, Yan Z, Tang Y.-C, Yang D, J. Org. Chem. 2003 68 6321
65. (y) Kasuya S, Kamijo S, Inoue M, Org. Lett. 2009 11 3630
66. (z) Schönecker B, Lange C, Zheldakova T, Gnther W, Grls H, Vaughan G, Tetrahedron 2005 61 103
67. (aa), Suzuki K, Oldenburg P D., Que L Jr., Angew. Chem. Int. Ed. 2008 47 1887
68. For selected reviews on CC bond formation directly from CH bonds, see
69. (a) Davies H M. L., Beckwith R E. J., Chem. Rev. 2003 103 2861
70. (b) Chen X, Engle K M., Wang D.-H, Yu J.-Q, Angew. Chem. Int. Ed. 2009 48 5094
71. (c) Mkhalid I A. I., Barnard J H., Marder T B., Murphy J M., Hartwig J F., Chem. Rev. 2010 110 890
72. Davis E, Croteau R, Cyclization Enzymes in the Biosynthesis of Monoterpenes Sesquiterpenes and Diterpenes, In Topics in Current Chemistry Vol. 209, Leeper F J., Vederas J C., Eds.; Springer-Verlag Berlin/Heidelberg 2000 53-95
73. (a) Chen K, Baran P S., Nature 2009 459 824
74. (b) Chen K, Ishihara Y, Morón Galán M, Baran P S., Tetrahedron 2010 66 4738
75. (a) Wu Q.-X, Shi Y.-P, Jia Z.-J, Nat. Prod. Rep. 2006 23 699
76. (b) De Marino S, Borbone N, Zollo F, Ianaro A, Di Meglio P, Iorizzi M, Planta Med. 2005 71 706
77. (c) Bedrossian A G., Beauchamp P S., Bernichi B, Dev V, Kitaw K Z., Rechtshaffen H, Bottini A T., Hope H, J. Essent. Oil Res. 2001 13 393
78. (d) Irwin M A., Geissman T A., Phytochemistry 1973 12 849
79. (e) Paknikar S K., Dhekne V V., Joshi G D., Indian J. Chem. 1977 15B 86
80. (f) Zhao P.-J, Li G.-H, Shen Y.-M, Chem. Biodiv. 2006 3 337
81. (g) Kim M K., Na M S., Hong J S., Jung S T., Hanguk Nonghwa Hakhoechi 1992 35 59
82. (h) Yukawa C, Iwabuchi H, Komemushi S, Sawabe A, J. Oleo. Sci. 2004 53 343
83. (i) Korthals H P., Merkel D, Muehlstaedt M, Justus Liebigs Ann. Chem. 1971 745 39
84. Chen K, Eschenmoser A, Baran P S., Angew. Chem. Int. Ed. 2009 48 9705
85. For the origin of the principle of divergent synthesis; see:, Boger D L., Brotherton C E., J. Org. Chem. 1984 49 4050
86. Wani M C., Taylor H L., Wall M E., Coggon P, McPhail A T., J. Am. Chem. Soc. 1971 93 2325
87. (a) Fuchs D A., Johnson R K., Cancer Treat. Rep. 1978 62 1219
88. (b) Schiff P B., Fant J, Horwitz S B., Nature 1979 277 665
89. (a) Nicolaou K C., Yang Z, Liu J J., Ueno H, Nantermet P G., Guy R K., Claiborne C F., Renaud J, Couladouros E A., Paulvannan K, Sorensen E J., Nature 1994 367 630
90. (b) Nicolaou K C., Nantermet P G., Ueno H, Guy R K., Couladouros E A., Sorensen E J., J. Am. Chem. Soc. 1995 117 624
91. (c) Nicolaou K C., Liu J J., Yang Z, Ueno H, Sorensen E J., Claiborne C F., Guy R K., Hwang C K., Nakada M, Nantermet P G., J. Am. Chem. Soc. 1995 117 634
92. (d) Nicolaou K C., Yang Z, Liu J J., Nantermet P G., Claiborne C F., Renaud J, Guy R K., Shibayama K, J. Am. Chem. Soc. 1995 117 645
93. (e) Nicolaou K C., Ueno H, Liu J J., Nantermet P G., Yang Z, Renaud J, Paulvannan K, Chadha R, J. Am. Chem. Soc. 1995 117 653
94. (f) Holton R A., Somoza C, Kim H B., Liang F, Biediger R J., Boatman P D., Shindo M, Smith C C., Kim S, J. Am. Chem. Soc. 1994 116 1597
95. (g) Holton R A., Kim H B., Somoza C, Liang F, Biediger R J., Boatman P D., Shindo M, Smith C C., Kim S, J. Am. Chem. Soc. 1994 116 1599
96. (h) Masters J J., Link J T., Snyder L B., Young W B., Danishefsky S J., Angew. Chem. Int. Ed. 1995 34 1723
97. (i) Danishefsky S J., Masters J J., Young W B., Link J T., Snyder L B., Magee T V., Jung D K., Isaacs R C. A., Bornmann W G., Alaimo C A., Coburn C A., Di Grandi M J., J. Am. Chem. Soc. 1996 118 2843
98. (j) Wender P A., Badham N F., Conway S P., Floreancig P E., Glass T E., Grnicher C, Houze J B., Jnichen J, Lee D, Marquess D G., McGrane P L., Meng W, Mucciaro T P., Mhlebach M, Natchus M G., Paulsen H, Rawlins D B., Satkofsky J, Shuker A J., Sutton J C., Taylor R E., Tomooka K, J. Am. Chem. Soc. 1997 119 2755
99. (k) Wender P A., Badham N F., Conway S P., Floreancig P E., Glass T E., Houze J B., Krauss N E., Lee D, Marquess D G., McGrane P L., Meng W, Natchus M G., Shuker A J., Sutton J C., Taylor R E., J. Am. Chem. Soc. 1997 119 2757
100. (l) Shiina I, Saitoh K, Frchard-Ortuno I, Mukaiyama T, Chem. Lett. 1998 27 3
101. (m) Mukaiyama T, Shiina I, Iwadare H, Saitoh M, Nishimura T, Ohkawa N, Sakoh H, Nishimura K, Tani Y.-i, Hasegawa M, Yamada K, Saitoh K, Chem. Eur. J. 1999 5 121
102. (n) Morihira K, Hara R, Kawahara S, Nishimori T, Nakamura N, Kusama H, Kuwajima I, J. Am. Chem. Soc. 1998 120 12980
103. (o) Kusama H, Hara R, Kawahara S, Nishimori T, Kashima H, Nakamura N, Morihira K, Kuwajima I, J. Am. Chem. Soc. 2000 122 3811
104. (p) Doi T, Fuse S, Miyamoto S, Nakai K, Sasuga D, Takahashi T, Chem. Asian J. 2006 1 370
105. For selected reviews in taxane isolation, see: (a) Baloglu E, Kingston D G. I., J. Nat. Prod. 1999 62 1448
106. (b) Hanson J R., Nat. Prod. Rep. 2000 17 165
107. (c) Hanson J R., Nat. Prod. Rep. 1993 10 159
108. (d) Miller R W., J. Nat. Prod. 1980 43 425
109. (e) Guritte-Voegelein F, Guénard D, Potier P, J. Nat. Prod. 1987 50 9
110. (f) Shigemori H, Kobayashi J, J. Nat. Prod. 2004 67 245
111. (g) Shi Q.-W, Kiyota H, Chem. Biodiv. 2005 2 1597
112. Koepp A E., Hezari M, Zajicek J, Vogel B S., LaFever R E., Lewis N G., Croteau R, J. Biol. Chem. 1995 270 8686
113. Hefner J, Rubenstein S M., Ketchum R E. B., Gibson D M., Williams R M., Croteau R, Chem. Biol. 1996 3 479
114. Li H, Horiguchi T, Croteau R, Williams R M., Tetrahedron 2008 64 6561
115. For a general treatment on combinatorials and permutations, see:, Bna M, Combinatorics of Permutations Chapman & Hall/CRC Boca Raton 2004
116. Compound 48 (as well as 24) has been previously obtained by total synthesis:, Rubenstein S M., Williams R M., J. Org. Chem. 1995 60 7215
117. Corey E J., Cheng X.-M, The Logic of Chemical Synthesis John Wiley & Sons New York 1989
118. (a) Bruggink A, Schoevaart R, Kieboom T, Org. Proc. Res. Dev. 2003 7 622
119. (b) Walji A M., MacMillan D W. C., Synlett 2007 1477
120. (a) Vazquez A, Williams R M., J. Org. Chem. 2000 65 7865
121. (b) Ahn Y M., VanderVelde D G., Georg G I., J. Org. Chem. 2002 67 7140
122. (c) Baldelli E, Battaglia A, Bombardelli E, Carenzi G, Fontana G, Gambini A, Gelmi M L., Guerrini A, Pocar D, J. Org. Chem. 2003 68 9773
123. (d) Horiguchi T, Cheng Q, Oritani T, Tetrahedron Lett. 2000 41 3907
124. (e) Horiguchi T, Nagura M, Cheng Q, Oritani T, Kudo T, Heterocycles 2000 53 2629
125. (f) Hoemann M Z., Velde D V., Aube J, Georg G I., Jayasinghe L R., J. Org. Chem. 1995 60 2918