Strategy and methodology development for the total synthesis of polyether ionophore antibiotics

Chemical Reviews

Volumn 100, Issue 6, 2000, Pages 2407-2473

  Faul, Margaret M ^a   Huff, Bret E ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; MOLECULAR STRUCTURE; MOLECULES; POLYETHERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALDOL REACTION; ESTER ENOLATE CLAISSEN REARRANGEMENT; IONOPHORES; JULIA OLEFINATION; POLYPROPIONATE; WITTING REACTION;

ANTIBIOTICS;

EID: 0033717307     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr940210s     Document Type: Article

References (245)

1. Polyether Antibiotics; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vols 1-2.
2. (a) Dutton, C. J.; Banks, B. J.; Cooper, C. B. Nat. Prod. Rep. 1994, 12, 165.
3. (b) Westley, J. W. J. Nat. Prod. 1986, 49, 35.
4. (c) Tao, R. C.; Crandall, L. W. Drugs Pharm. Sci. 1994, 63, 1.
5. For earlier reviews on the total synthesis of polyether ionophores, see: (a) Yonemitsu, O.; Horita, K. Recent Progress in the Chemistry of Synthetic Antibiotics; Lukacs, Gabor, Ohno, Masaji, Eds.; Springer: Berlin, 1990; p 447.
6. (b) Ireland, R. E. Aldrichim. Acta 1988, 21, 59.
7. (c) Still, W. C.; Cai, D.; Lee, D.; Hauck, P.; Bernardi, A.; Romero, A. Lect. Heterocycl. Chem. 1987, 9, 33.
8. (d) Yonemitsu, O.; Horita, K.; Noda, I.; Oikawa, Y. Lect. Heterocycl. Chem. 1987, 9, 105.
9. (e) Kishi, Y.; Hatakeyama, S.; Lewis, M. D. Front. Chem., Plenary Keynote Lect. IUPAC Congr., 28th; Laidler, K. J., Ed.; Pergamon: Oxford, U.K., 1982; p 287.
10. (f) Kishi, Y. Aldrichim. Acta 1980, 13, 23.
11. For an excellent review on the use of A-1,3 interactions in synthesis, see: (a) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
12. The chemistry of the SAE reaction has been well reviewed, see: (a) Pfenninger, A. Synthesis 1986, 89.
13. (b) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1.
14. (c) For a review of synthetic aspects and applications of the asymmetric epoxidation reaction, see: Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, FL, 1983; Vol 5, Chapter 7.
15. (d) For a review on the mechanism of the asymmetric epoxidation reaction, see: Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, Florida, 1983; Vol 5, Chapter 8.
16. For general reviews on Cram selectivity and the aldol reaction, see: (a) Nielsen, A. T.; Houlihan, W. J. Org. React. 1968, 16, 438.
17. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
18. (c) Mukaiyama, T. Org. React. 1982, 28, 203.
19. (d) Heathcock, C. H. Curr. Trends Org. Synth., Proc. Int. Conf. Nozaki, 4th ed.; Hitosi., Ed.; Pergamon: Oxford, U.K., 1983; p 27.
20. (e) Heathcock, C. H. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, FL, 1984; Vol 3, p 111.
21. (f) Eliel, E. L. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, FL, 1983; 2, p 125.
22. (g) Reetz, M. T. Angew. Chem., Intl. Ed. Engl. 1984, 23, 556.
23. (h) Heathcock, C. H. Stud. Org. Chem. (Amsterdam) 1984, 5B (Compr. Carbanion Chem., Pt. B), p 177.
24. (i) Reetz, M. T. Pure Appl. Chem. 1988, 60, 1607.
25. (j) Mulzer, J. Organic Synthesis Highlights; VCH: Weinheim, 1991; p 3.
26. (k) Eliel, E. L.; Frye, S. V.; Hortelano, E. R.; Chen, X.; Bai, X. Pure Appl. Chem. 1991, 63, 1591.
27. (l) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
28. (m) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
29. (n) Fleming, I. J. Chem. Soc., Perkin Trans. 1 1992, 3363.
30. (o) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317.
31. (p) Hoffmann, R. W. Stereocontrolled Organic Synthesis; Trost, B. M., Ed.; Blackwell, Oxford, U.K., 1994; p 259.
32. (q) Mukaiyama, T. Aldrichim. Acta 1996, 293, 59.
33. Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933.
34. (a) Fukuyama, T.; Vranesic, B.; Negri, D. P.; Kishi, Y. Tetrahedron Lett. 1978, 2741.
35. (b) Nakata, T.; Kishi, Y. Tetrahedron Lett. 1978, 2745.
36. These methods have been thoroughly reviewed in the context of natural product synthesis, see: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3.
37. (b) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
38. For a comprehensive review on haloetherification and related reactions, see: (c) Cardillo, G.; Orena, M Tetrahedron 1990, 46, 3321.
39. In general, yields for reactions were provided whenever they were available from the text of the original paper.
40. No experimental details on the aldol coupling and transformation to isolasalocid A have been published.
41. (a) Schmid G.; Fukayama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 259.
42. (b) Fukuyama, T.; Wang, C. L. J. Kishi, Y. J. Am. Chem. Soc. 1979, 101, 260.
43. (c) Fukuyama, T. Akasaka, K.; Karanewsky, D. S.; Wang, C. L. J.; Schmid, G. Kishi, Y. J. Am. Chem. Soc. 1979, 101, 262.
44. (d) Kishi, Y. Lect. Heterocycl. Chem. 1980, 5, S95.
45. For an alternative approach, see: Danishefsky, S.; Harvey, D. F. J. Am. Chem. Soc. 1985, 107, 6647.
46. An alternative approach to the B-C ring system and spiroketal of monensin A was described by Walba, see: (a) Walba, D. M.; Edwards, P. D. Tetrahedron Lett. 1980, 21, 3531.
47. (b) Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046.
48. (c) Walba, D. M.; Wand, M. D. Tetrahedron Lett. 1982, 23, 4995.
49. (a) Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031.
50. (b) Still, W. C.; Schneider, J. A. Tetrahedron Lett. 1980, 21, 1035.
51. (a) Collum, D. B.; McDonald, J. H.; Still, W. C. J. Am. Chem. Soc. 1980, 102, 211.
52. (b) Collum, D. B.; McDonald, J. H.; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2120.
53. Evans, D. A.; Sacks, C. E.; Kleschick, W. A.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789.
54. Evans, D. A.; Sacks, C. E.; Whitney, R. A.; Mandel, N. G. Tetrahedron Lett. 1978, 19, 727.
55. For an extensive discussion, see: Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983.
56. An independent model study by Sondheimer and co-workers supported the predominant formation of the desired dioxaspiro ring system, see: Probert, C. L.; Sondheimer, F. Tetrahedron Lett. 1978, 19, 3955.
57. Subsequently, Deslongchamps reported a similar cyclization, see: (a) Deslongchamps, P.; Rowan, D. D.; Pothier, N.; Sauvé, G.; Saunders, J. K. Can. J. Chem. 1981, 59, 1105.
58. (b) Pothier, N.; Rowan, D. D.; Deslongchamps, P.; Saunders: J. K. Can. J. Chem. 1981, 59, 1132.
59. (c) Deslongchamps, P.; Pothier, N. Can. J. Chem. 1990, 68, 597.
60. For reviews on Claisen rearrangements, see: (a) Ziegler, F. E. Acc. Chem. Res. 1977, 10, 227.
61. (b) Bennett, G. B. Synthesis 1977, 589.
62. (a) Ireland, R. E. Aldrichim. Acta 1980, 21, 59.
63. (b) Ireland, R. E.; Thaisrivongs, S.; Wilcox, C. S. J. Am. Chem. Soc. 1980, 102, 1155.
64. (a) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
65. (b) Ireland, R. E.; Anderson, R. C.; Badoud, R.; Fitzsimmons, B. J.; McGarvey, G. J.; Thaisrivongs, S.; Wilcox, C. S. J. Am. Chem. Soc. 1983, 105, 1988.
66. Ireland also reported a total synthesis of the enantiomer of lasalocid A, see: Ireland, R. E.; Courtney, L.; Fitzsimmons, B. J. J. Am. Chem. Soc. 1983, 48, 5186.
67. (a) Nicolaou, K. C.; Magolda, R, L. J. Org. Chem. 1981, 46, 1506.
68. (b) Nicolaou, K. C.; Papahatjis, D. P.; Claremon, D. A.; Dolle, R. E., III. J. Am. Chem. Soc. 1981, 103, 6967.
69. (c) Nicolaou, K. C.; Papahatjis, D. P.; Claremon, D. A.; Magolda, R. L.; Dolle, R. E. J. Org. Chem. 1985, 50, 1440.
70. (a) Enders, D.; Eichenauer, H. Chem Ber. 1979, 112, 2933.
71. (b) Enders, D.; Eichenauer, H. Tetrahedron Lett. 1977, 191.
72. 8 fragment of indanomycin, see: Whitney, R. A. Can. J. Chem. 1986, 64, 803.
73. (a) Kishi, Y.; Hatakeyama, S.; Lewis, M. D. Front. Chem., Plenary Keynote Lect. IUPAC Congr., 28th; Laidler, K. J., Ed; Pergamon: Oxford, U.K., 1982; p 287.
74. (b) Kishi, Y. Aldichim. Acta 1980, 13, 23.
75. (c) Tino, J. A.; Lewis, M. D.; Kishi, Y. Heterocycles 1987, 25, 97.
76. (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 4343.
77. (b) Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347.
78. (c) Hasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 21, 4229.
79. (c) Kishi, Y. Aldrichim. Acta 1980, 13, 23.
80. 7 tetrahydropyran, see: Tino, J. A.; Lewis, M. A.; Kishi, Y. Heterocycles 1987, 25, 97.
81. 9 fragment of salinomycin, although no details of this synthesis have been published.
82. 24 fragment of lasalocid A and isolasalocid A is undoubtedly applicable.
83. Martinez, G. R.; Grieco, P. A.; Williams, E.; Kanai, K.; Srinivasan, C. V. J. Am. Chem. Soc. 1982, 104, 1436.
84. (a) Edwards, M. P.; Ley, S. V.; Lister, S. G. Tetrahedron Lett. 1981, 22, 361.
85. (b) Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D. J. Chem. Soc., Chem. Commun. 1983, 630.
86. (c) Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D.; Williams, D. J. J. Org. Chem. 1984, 49, 3503.
87. (a) Kocienski, P. J.; Lythgoe, B.; Waterhouse, I. J. Chem. Soc., Perkin Trans. 1 1980, 1045.
88. (b) Kocienski, P. J.; Lythgoe, B. J. Chem. Soc., Perkin Trans. 1 1980, 1400.
89. (c) Kocienski, P. J.; Lythgoe, B.; Roberts, D. A. J. Chem. Soc., Perkin Trans 1 1978, 834.
90. (d) Kocienski, P. J.; Lythgoe, B.; Ruston, S. J. Chem. Soc., Perkin Trans 1 1978, 829.
91. (a) Roush, W. R.; Myers, A. G. J. Org. Chem. 1981, 46, 1509.
92. (b) Roush, W. R.; Peseckis, S. M. Tetrahedron Lett. 1982, 23, 4879.
93. (c) Roush, W. R.; Peseckis, S. M.; Walts, A. E. J. Org. Chem. 1984, 49, 3432.
94. Roush, W. R.; Adam, M. A.; Harris, D. J. J. Org. Chem. 1985, 50, 2000.
95. (a) Nakahara, Y.; Fujita, A.; Beppu, K.; Ogawa, T. Tetrahedron 1986, 42, 6465.
96. (b) Nakahara, Y.; Fujita, A.; Ogawa, T. Agric. Biol. Chem. 1985, 49, 1491.
97. (c) Nakahara, Y.; Fujita, A.; Ogawa, T. J. Carbohydr. Chem. 1984, 3, 487.
98. Boeckman, R. K., Jr.; Enholm, E. J.; Demko, D. M.; Charette, A. B. J. Org. Chem. 1986, 51, 4743.
99. Negri, D. P.; Kishi, Y. Tetrahedron Lett. 1987, 28, 1063.
100. It was not determined whether the reaction actually took place under kinetic or thermodynamic control.
101. (a) Boeckman, R. K., Jr.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1987, 109, 7553.
102. (b) Boeckman, R. K., Jr.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1991, 113, 5337.
103. (a) Danishefsky, S. J.; Selnick, H. G.; Zelle, R. E.; DeNinno, M. P. J. Am. Chem. Soc. 1987, 109, 1572.
104. (b) Danishefsky, S. J.; Selnick, H. G.; Zelle, R. E.; DeNinno, M. P. J. Am. Chem. Soc. 1988, 110, 4368.
105. A number of groups have reported the synthesis of fragments of zincophorin, see: (a) Chemler, S. R.; Roush, W. R. J. Org. Chem. 1998, 63, 3800.
106. (b) Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1998, 63, 3701.
107. (c) Booysen, J. F.; Holzapfel, C. W. Synth. Commun 1995, 25, 1473.
108. (d) Balestra, M.; Wittman, M. D.; Kallmerten, J. Tetrahedron Lett. 1988, 29, 6905.
109. (e) Cywin, C. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 1103.
110. (a) Danishefsky, S. J. Aldrichim. Acta 1986, 19, 59.
111. (b) Danishefsky, S. J.; DeNinno, M. P. Angew Chem., Int. Ed. Engl. 1987, 26, 15.
112. (a) Luche, J. L.; Gamal, A. L. J. Am. Chem. Soc. 1979, 101, 5848.
113. (b) Ferrier, R. J. Chem. Soc. 1964, 5443.
114. Danishefsky, S. J.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803.
115. Zelle, R. E.; DeNinno, M. P.; Selnick, H. G.; Danishefsky, S. J. J. Org. Chem. 1986, 51, 5032.
116. Gennari, C.; Bernardi, A.; Colombo, L.; Scolastico, C. J. Am. Chem. Soc. 1985, 107, 5812.
117. Gennari, C.; Colombo, L.; Bertolini, G.; Schimperna, G. J. Org. Chem. 1987, 52, 2754.
118. Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 0, 2506.
119. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
120. Evans, D. A.; Bartroli, J. A.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
121. For a review of chelate control in addition reactions of α- and β-alkoxy carbonyl compounds, see: Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
122. Evans, D. A.; Bender, S. L. Tetrahedron Lett. 1986, 27, 799.
123. (a) Horita and Yonemitsu reported a formal total synthesis of salinomycin in 1987, see: Yonemitsu, O.; Horita, K.; Noda, I.; Oikawa, Y. Lect. Heterocycl. Chem. 1987, 9, S105.
124. (b) Horita, K.; Oikawa, Y.; Yonemitsu, O. Chem. Pharm. Bull. 1989, 37, 1698.
125. (c) Horita, K.; Nagato, S.; Oikawa, Y.; Yonemitsu, O. Chem. Pharm. Bull. 1989, 37, 1705.
126. (d) Horita, K.; Oikawa, Y.; Nagato, S.; Yonemitsu, O. Chem. Pharm. Bull. 1989, 37, 1717.
127. (e) Horita, K.; Nagato, S.; Oikawa, Y.; Yonemitsu, O. Chem. Pharm. Bull. 1989, 37, 1726.
128. (f) Horita, K.; Nagato, S.; Oikawa, Y.; Yonemitsu, O. Tetrahedron Lett. 1987, 28, 3253.
129. (g) Horita, K.; Oikawa, Y.; Nagato, S.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 5143.
130. (h) Oikawa, Y.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1985, 26, 1541.
131. (a) Oikawa, Y.; Nishi, T.; Itaya, H.; Yonemitsu, O. Tetrahedron Lett. 1983, 24, 1987.
132. (b) Oikawa, Y.; Tanaka, T.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1984, 25, 5397.
133. Oikawa, Y.; Tanaka, T.; Horita, K.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1984, 25, 5393.
134. 20 alcohol into an unsaturated spiroketal via allylic oxidation, see: Brimble, M. A.; Edmonds, M. K.; Williams, G. M. Tetrahedron Lett. 1990, 31, 7509.
135. Brimble reported a synthesis of the D-E ring of salinomycin by olefin epoxidation, acid-catalyzed cyclization to a tetrahydrofuran, followed by ring expansion to the E-ring tetrahydropyran, see: Brimble, M. A.; Prabaharan, H. Tetrahedron 1998, 54, 2113.
136. Brimble reported the synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin, see: Brimble M, A.; Williams, G. M. J. Org. Chem. 1992, 57, 5818.
137. Ziegler, F. E.; Cain, W. T. J. Org. Chem. 1989, 54, 3347.
138. Ziegler, F. E.; Kneisley, A.; Thottathil, J. K.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5434.
139. (a) Criegee, R. Chem. Ber. 1944, 77, 722.
140. (b) Criegee, R.; Kaspar, R. Justus. Liebigs Ann. Chem. 1948, 560, 127.
141. (a) Horita and Yonemitsu reported a formal total synthesis of lasalocid A and isolasalocid A in 1987, see ref 57a.
142. (b) Noda, I.; Horita, K.; Oikawa, Y.; Yonemitsu, O. Tetrahedron Lett. 1990, 31, 6035.
143. (c) Horita, K.; Noda, I.; Tanaka, K.; Miura, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron, 1993, 49, 5979.
144. (d) Horita, K.; Noda, I.; Tanaka, K.; Oikawa, Y.; Yonemitsu, O. Tetrahedron, 1993, 49, 5997.
145. (e) Horita, K.; Noda, I.; Tanaka, K.; Miura, T.; Yonemitsu, O. Heterocycles 1990, 30 (1, special issue), 321.
146. Horita, K.; Tanaka, K.; Yonemitsu, O. Chem. Pharm. Bull. 1993, 41, 2044.
147. M139603 is the only other ion-selective ionophore that contains a β-dicarbonyl moiety as part of its tetronic acid residue, see: Davies, D. H.; Snape, E. W.; Suter, P. J.; King, T. J.; Falshaw, C. P. J. Chem. Soc., Chem. Commun. 1981, 1073.
148. Evans, D. A.; Dow, R. L.; Shih, T. L.; Takacs, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5290.
149. 15 fragment using carbohydrates as templates for the stereoselective construction of the syn-or anti-1,3-dimethyl unit, see: Nicoll-Griffith, D. A.; Weiler, L. Tetrahedron 1991, 47, 2733.
150. 6 methyl stereocenters by acid-catalyzed equilibration of the carbon centers α to a spiroketal. Methodology similar to that was employed by Evans in his synthesis of calcimycin, see: Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 5303.
151. 16 fragment by enzymatic Baeyer-Villiger oxidation, see: Taschner, M. J.; Chen, Q. Z. Bioorg. Med. Chem. Lett. 1992, 1, 535.
152. 22 fragment by application of cyclic stereocontrol in the nucleophilic ring opening of oxabicyclic[3.2.1] compounds, see: (a) Lautens, M.; Chiu, P.; Colucci, J. T. Angew. Chem., Int. Ed. Engl. 1993, 32, 281.
153. (b) Lautens, M. Pure Appl. Chem. 1992, 64, 1873.
154. 2-catalyzed epoxidation, see: Von der Emde, H.; Langels, A.; Noltemeyer, M.; Bruckner, R. Tetrahedron Lett. 1994, 35, 7609.
155. 22 fragment of ionomycin, see: Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; Renaud, J.; Robinson, G.; Lavallée, J.-F.; Slassi, A.; Jung, G.; Rancourt, J.; Durkin, K.; Liotta, D. J. Org. Chem. 1994, 59, 1166.
156. Evans, D. A.; Dow, R. L. Tetrahedron Lett. 1986, 27, 1007.
157. 32 fragment of ionomycin by a stereoselective permanganate-induced cyclization of a 10 carbon Z,Z-dienic ester, followed by separation of the O-acetyl-(S)-mandelate esters, see: Spino, C.; Weiler, L. Tetrahedron Lett. 1987, 28, 731.
158. 32 tetrahydrofuran segement of ionomycin, see: Wuts, P. G. M.; D'Costa, R.; Butler, W. J. Org. Chem. 1984, 49, 2582.
159. Hanessian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276.
160. Sereg, D. Chemtracts: Org. Chem. 1990, 3, 458.
161. (a) Hanessian, S. Aldrichim. Acta 1988, 22, 3 and references therein.
162. (b) Hanessian, S. In Total Synthesis of Natural Products: The Chiron Approach; Baldwin, J. E., Ed.; Pergamon Press: Oxford, 1983.
163. (c) Hanessian, S.; Murray, P. J. Tetrahedron 1987, 43, 5055.
164. (d) Hanessian, S.; Murray, P. J. Can. J. Chem. 1986, 64, 2231.
165. (e) Hanessian, S.; Murray, P. J.; Sahoo, S. P. Tetrahedron Lett. 1985, 26, 5627.
166. Evans, D. A.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mathre, D. J. J. Am. Chem. Soc. 1991, 113, 7613.
167. Evans, D. A.; Polniaszek, R. P. Tetrahedron Lett. 1986, 27, 5683.
168. (a) Kotecha, N. R.; Ley, S. V.; Mantegani, S. Synlett 1992, 395.
169. (b) Díez-Martin, D.; Koetcha, N. R.; Ley, S. V.; Menéndez, J. C. Synlett 1992, 399.
170. (c) Díez-Martin, D.; Kotecha, N. R.; Ley, S. V.; Mantegani, S.; Menéndez, J. C.; Organ, H. M.; White, A. D.; Banks, B. J. Tetrahedron 1992, 48, 7899.
171. For a review on the application of tricarbonyliron lactone complexes in organic synthesis, see: Ley, S. V. Pure. Appl. Chem. 1994, 66, 1415.
172. Ley, S. V.; Lygo, B.; Sternfeld, F.; Wonnacott, A. Tetrahedron 1986, 42, 4333.
173. 20 spiroketal of routiennocin, see: Yadav, J. S.; Muralidhar, B. Tetrahedron Lett. 1998, 39, 2867.
174. (a) Horita, K.; Inoue, T.; Tanaka. K.; Yonemitsu, O. Tetrahedron Lett. 1992, 33, 5537.
175. (b) Horita, K.; Tanaka, K.; Inoue, T.; Yonemitsu, O. Tetrahedron Lett. 1992, 33, 5541.
176. (c) Horita, K.; Inoue, T.; Tanaka, K.; Yonemitsu, O. Tetrahedron 1996, 52, 531.
177. (d) Horita, K.; Tanaka, K.; Inoue, T.; Yonemitsu, O. Tetrahedron 1996, 52, 551.
178. Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487.
179. Oikawa, Y.; Tanaka, T.; Horita, K.; Noda, I.; Nakajima, N.; Kakusawa, N.; Hamada, T.; Yonemitsu, O. Chem. Pharm. Bull. 1987, 35, 2184.
180. The use of highly functionalized epoxides, derived from asymmetric tris(hydroxymethyl)methane, to the synthesis of fragments of lasalocid A and related ionophores has been reported, see: Guanti, G.; Narisano, E. Tetrahedron 1996, 52, 12631.
181. (a) Hori, K.; Hikage, N.; Inagaki, A.; Mon, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888.
182. (b) Hori, K.; Nomura, K.; Hikage, N.; Yoshii, E. Chem Pharm. Bull. 1990, 38, 1778.
183. (c) Hori, K.; Nomura, K.; Hikage, N.; Yoshii, E. Chem Pharm. Bull. 1990, 38, 1781.
184. (d) Hori, K.; Nomura, K.; Hikage, N.; Yoshii, E. J. Chem. Soc., Chem. Commun. 1989, 11, 712.
185. (e) Hori, K.; Nomura, K.; Yoshii, E. Heterocycles 1989, 29, 663.
186. Ley prepared a highly functionalized precursor to tetronomycin and tetronasin, see: (a) Ley, S. V.; Clase, J. A.; Mansfield, D. J.; Osborn, H. M. I. J. Heterocycl. Chem. 1996, 33, 1533.
187. (b) Boons, G. J.; Brown, D. S.; Clase, J. A.; Lennon, I. C.; Ley, S. V. Tetrahedron Lett. 1994, 35, 319.
188. (c) Boons, G. J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323.
189. (d) De Laszlo, S. E.; Ford, M. J.; Ley, S. V.; Maw, G. N. Tetrahedron Lett. 1990, 31, 5525.
190. (e) Ley, S. V.; Maw, G. N.; Trudell, M. L. Tetrahedron Lett. 1990, 31, 5521.
191. (f) Ley, S. V.; Wadsworth, D. J. Tetrahedron Lett. 1989, 30, 1001.
192. (g) Doherty, A. M.; Ley, S. V. Tetrahderon Lett. 1986, 27, 105.
193. 13 fragment and its enantiomer, see: Hori, K.; Mori, S.; Nomura, K.; Inagaki, A.; Yoshii, E. Chem. Pharm. Bull. 1990, 38, 1784.
194. Semmelhack reported a synthesis of the tetrahydropyran ring using palladium(II) chemistry, see: Semmelhack, M. F.; Kim, C. R.; Dobler, W.; Meier, M. Tetrahedron Lett. 1989, 30, 4925.
195. 27 fragment, see: (a) Lee, H. W.; Lee, I. Y. C. Synlett 1991, 871.
196. (b) Lee, H. W.; Lee, I. Y. C.; Kim, S. K. Tetrahedron Lett. 1990, 31, 7637.
197. Semmelhack reported a synthesis of the trans-2,5-substituted tetrahydrofuran of tertonomycin by palladium(II)-catalyzed intramolecular addition of a hydroxyl group to an alkene, see: Semmelhack, M. F.; Epa, W. R.; Cheung, A. W.-H.; Gu, Y.; Kim, C.; Zhang, N.; Lew, W. J. Am. Chem. Soc. 1994, 116, 7455.
198. Lewis, M. D.; Chu, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
199. 28 fragment, see: Hori, K.; Nomura, K.; Hikage, N.; Yoshii, E. Chem. Pharm. Bull. 1990, 38, 1781.
200. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183.
201. (a) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7166.
202. (b) Ireland, R. E.; Armstrong, J. D.; Lebreton, J.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7152.
203. (c) Ireland, R. E.; Norbeck, D. W. J. Am. Chem. Soc. 1985, 107, 3279.
204. (d) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285
205. (e) Ireland, R. E.; Maienfisch, P. J. Org. Chem. 1988, 53, 640.
206. (f) Ireland, R. E.; Häbich, D.; Norbeck, D. W. J. Am. Chem. Soc. 1985, 107, 3271.
207. (a) Burke, S, D.; Armistead, D. M.; Shankaran, K. Tetrahedron Lett. 1986, 27, 6295.
208. (b) Burke, S. D.; Piscopio, A. D.; Kort, M. E.; Matulenko, M. A.; Parker, M. H.; Armistead, D. M.; Shankaran, K. J. Org. Chem. 1994, 59, 332.
209. For general reviews of this topic, see: (a) Mitchell, T. N. Synthesis 1992, 803.
210. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
211. (a) Burke, S. D.; Armistead, D. M.; Schoenen, F. J. J. Org. Chem. 1984, 49, 4320.
212. (b) Burke, S. D.; Armistead, D. M.; Schoenen, F.; Fevig, J. M. Tetrahedron 1986, 42, 2787.
213. (c) Burke, S. D.; Armistead, D. M.; Fevig, J. M. Tetrahedron Lett. 1985, 26, 1163.
214. 7 fragment of indanomycin, see: Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082.
215. (a) Suzuki, M.; Yanagisawa, A.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 4718.
216. (b) Noyori, R., Suzuki, M. Chemtracts: Org. Chem. 1990, 3, 173.
217. (a) Miyake, H.; Yamamura, K. Chem Lett. 1989, 989.
218. (b) Zhang, H.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
219. (a) Kocienski, P. J.; Brown, R. C. D.; Pommier, A.; Procter, M.; Schmidt, B. J. Chem. Soc., Perkin Trans 1, 1998, 1, 9.
220. (b) Brown, R. C. D.; Kocienski, P. Spec. Publ. R. Soc. Chem. 1997, 198 (anti-infectives), 42.
221. For reviews on the chemistry of spiroketals, see: (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
222. (b) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
223. (c) Kluge, A. F. Heterocycles 1986, 24, 1699.
224. Kocienski developed an alternative approach to the dispiroacetal moiety via oxidative rearrangement of an acyl furan. However, this approach was less efficient and less stereoselective than the allenol ether route, see: (a) Kocienski, P.; Fall, Y.; Whitby, R. J. Chem. Soc., Perkin Trans. 1 1989, 4, 841.
225. (b) Brown, R. C. D.; Kocienski, P. J. Synlett 1994, 6, 415.
226. (c) Brown, R. C. D.; Kocienski, P. Synlett 1994, 6, 417.
227. For methodology on the synthesis of oxidized spiroketals by oxidation-rearrangement of 2-furyl ketones, see: Perron, F.; Albizati, K. F. J. Org. Chem. 1989, 54, 2044.
228. Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670.
229. (a) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418.
230. (b) Nagao, Y.; Kumagai, T.; Yamada, S.; Fujita, E.; Inoue, Y.; Nagasa, Y.; Aoyagi, S.; Abe, T. J. Chem. Soc., Perkin Trans. 1 1985, 2361.
231. Brimble has reported a synthesis of lactone 374 using Evans' chiral imide enolate methodology, see: Brimble, M. A. Aust. J. Chem. 1990, 43, 1035.
232. Klein, E.; Rojahn, W. Tetrahedron 1965, 21, 2353.
233. Walba, D. M.; Przybyla, C. A.; Walker, C. B., Jr. J. Am. Chem. Soc. 1990, 112, 5624.
234. Oppolzer, W. Tetrahedron 1987, 43, 1969.
235. Baldwin, J. E.; Crossley, M. J.; Lehtonen, E.-M. M. J. Chem. Soc., Chem Commun. 1979, 918.
236. Walba proposed an alternative mechanism for the oxidative cyclization reaction, see: Walba, D. M.; Wand, M. D.; Wilkes, M. C. J. Am. Chem. Soc. 1979, 101, 4396.
237. (a) Evans, D. A.; Ratz, A. R.; Huff, B. E.;Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448.
238. (b) Evans, D. A.; Ratz, A. R.; Huff, B. E.; Sheppard, G. S. Tetrahedron Lett. 1994, 35, 7171.
239. Still, W. C.; Romero, A. G. J. Am. Chem. Soc. 1986, 108, 2105.
240. Schreiber, S. L.; Sammakia, T.; Hulin, B.; Schulte, G. J. Am. Chem. Soc. 1986, 108, 6.
241. Evans, D. A.; Sheppard, G. S. J. Org. Chem. 1990, 55, 5192.
242. Vedejs, E.; Gapinski, D. M. J. Am. Chem. Soc. 1983, 105, 5058.
243. 21 fragment of monensin A, see: McDonald, F. E.; Schultz, C. C. Tetrahedron 1997, 53, 16435.
244. For a detailed discussion of chelate-controlled carbonyl addition, see: Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778.
245. For a review on directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.