Dead ends and detours en route to total syntheses of the 1990s

Angewandte Chemie - International Edition

Volumn 39, Issue 9, 2000, Pages 1538-1559

  Sierra, Miguel A ^a   De La Torre, Maria C ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Natural products; Protecting groups; Synthesis design; Synthetic methods; Total synthesis

Indexed keywords

FUNCTIONAL GROUP; NATURAL PRODUCT; ORGANIC COMPOUND;

CHEMICAL MODIFICATION; CYCLIZATION; MODEL; ORGANIC CHEMISTRY; REVIEW; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 0034595260     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(20000502)39:9<1538::aid-anie1538>3.0.co;2-o     Document Type: Review

References (123)

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2. For a compendium of some of the most beautiful syntheses ever carried out, see a) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, Wiley-VCH, Weinheim, 1996; b) K. C. Nicolaou, D Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122.
3. For a compendium of some of the most beautiful syntheses ever carried out, see a) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, Wiley-VCH, Weinheim, 1996; b) K. C. Nicolaou, D Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122.
4. See, for example D. Seebach, Angew. Chem. 1990, 102, 1363-1409; Angew. Chem. Int. Ed. Engl. 1990, 29, 1320-1367; for a different perspective about the maturity of organic synthesis see the Epilogue section of the following review by Heathcock: C. H. Heathcock, Angew. Chem. 1992, 104, 675-691; Angew. Chem. Int. Ed. Engl. 1992, 31, 665-681.
5. See, for example D. Seebach, Angew. Chem. 1990, 102, 1363-1409; Angew. Chem. Int. Ed. Engl. 1990, 29, 1320-1367; for a different perspective about the maturity of organic synthesis see the Epilogue section of the following review by Heathcock: C. H. Heathcock, Angew. Chem. 1992, 104, 675-691; Angew. Chem. Int. Ed. Engl. 1992, 31, 665-681.
6. See, for example D. Seebach, Angew. Chem. 1990, 102, 1363-1409; Angew. Chem. Int. Ed. Engl. 1990, 29, 1320-1367; for a different perspective about the maturity of organic synthesis see the Epilogue section of the following review by Heathcock: C. H. Heathcock, Angew. Chem. 1992, 104, 675-691; Angew. Chem. Int. Ed. Engl. 1992, 31, 665-681.
7. See, for example D. Seebach, Angew. Chem. 1990, 102, 1363-1409; Angew. Chem. Int. Ed. Engl. 1990, 29, 1320-1367; for a different perspective about the maturity of organic synthesis see the Epilogue section of the following review by Heathcock: C. H. Heathcock, Angew. Chem. 1992, 104, 675-691; Angew. Chem. Int. Ed. Engl. 1992, 31, 665-681.
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10. For a perspective on homogenous catalysis, see a) W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074-1095; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048-1067; selected reviews: b) E. J. Corey, A. Guzman-Pérez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
11. For a perspective on homogenous catalysis, see a) W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074-1095; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048-1067; selected reviews: b) E. J. Corey, A. Guzman-Pérez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
12. For a perspective on homogenous catalysis, see a) W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074-1095; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048-1067; selected reviews: b) E. J. Corey, A. Guzman-Pérez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
13. For a perspective on homogenous catalysis, see a) W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074-1095; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048-1067; selected reviews: b) E. J. Corey, A. Guzman-Pérez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
14. For a perspective on homogenous catalysis, see a) W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074-1095; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048-1067; selected reviews: b) E. J. Corey, A. Guzman-Pérez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
15. For a perspective on homogenous catalysis, see a) W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074-1095; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048-1067; selected reviews: b) E. J. Corey, A. Guzman-Pérez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; c) D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
16. a) J. M. Thomas, Angew. Chem. 1994, 106, 963-989; Angew. Chem. Int. Ed. Engl. 1994, 33, 913-937; b) see also the thematic issue of Chemical Reviews dedicated to heterogenous catalysis: Chem. Rev. 1995, 95, 475-788.
17. a) J. M. Thomas, Angew. Chem. 1994, 106, 963-989; Angew. Chem. Int. Ed. Engl. 1994, 33, 913-937; b) see also the thematic issue of Chemical Reviews dedicated to heterogenous catalysis: Chem. Rev. 1995, 95, 475-788.
18. a) J. M. Thomas, Angew. Chem. 1994, 106, 963-989; Angew. Chem. Int. Ed. Engl. 1994, 33, 913-937; b) see also the thematic issue of Chemical Reviews dedicated to heterogenous catalysis: Chem. Rev. 1995, 95, 475-788.
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20. b) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2488; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) See also the thematic issue of Chemical Reviews dedicated to combinatorial chemistry: Chem. Rev. 1997, 97, 347-509.
21. b) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2488; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) See also the thematic issue of Chemical Reviews dedicated to combinatorial chemistry: Chem. Rev. 1997, 97, 347-509.
22. b) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2488; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; c) See also the thematic issue of Chemical Reviews dedicated to combinatorial chemistry: Chem. Rev. 1997, 97, 347-509.
23. One reviewer of this review pointed out two additional reasons not to go into details about failures: first: "failed" reactions often lead to results that are not clean. These are usually described in papers as giving "decomposition of starting materials" or "complex mixtures of products". For those involved in Organic Synthesis such reactions seem to occur far too often! From such experiments conclusive and/or publishable information is difficult to glean. Reporting of results in this fashion, while being honest, does not provide much information from which the reader can learn and is often avoided. Second: often Organic Synthesis relies on luck! It doesn't matter how well planned a synthesis is, the route is nearly always going to have stages which are risky and predictably so in advance. Such risks are assessed in the planning stages before undertaking synthetic work. It may sometimes be judged that a very high-risk strategy may offer significant potential benefits which warrant investigation. Failures of high-risk work may go unreported as with the benefit of hindsight they may look to have strayed across the border between courageous and foolish!
24. There are, of course, other points of view for not reporting excessive details about failures. The words written by Danishefsky two years ago are fully illustrative: Before relating a few of these episodes [referring to the synthesis of some of the many molecules synthesized in his group], some important cautionary notes and attributions are in order. For those schooled in the art (of Organic Synthesis), there will be little need for either. The experienced practitioner is well aware that the pathways of synthesis are circuitous, bumpy, and even treacherous. Seldom do straight lines suffice to connect points in a synthesis of real consequence. Hence, the seasoned chemist will appreciate that along with these "magic moments" of success, one could have reported a litany of setbacks and reversals. However, for younger and more optimistic enthusiasts, it is appropriate to underscore the uncertainties, the detours and, yes, the frustrations associated with Organic Synthesis. Success is often a prize reserved for those who temper noble ideas with appropriate measures of realism and skepticism. Given the episodic nature of our science, wisdom may well be more valuable than cleverness, the ability to plumb the implications of each experiment, positive and negative, is central to the process of learning as we go along. Our quest to reach the promised land should not render us insensitive to opportunities for discovery, even as we find our way through the desert. See: S. J. Danishefsky, Tetrahedron 1997, 53, 8689-8730.
25. K. C. Nicolaou, C. K. Hwang, M. E. Duggan, D. A. Nugiel, Y. Abe, K. B. Reddy, S. A. DeFrees, D. R. Reddy, R. A. Awartani, S. R. Conley, F. P. J. T. Rutjes, E. A. Theodorakis, J. Am. Chem. Soc. 1995, 117, 10227-10238. See Ref. [1a)], p 750-752, for a careful discussion of this approach to brevetoxin B.
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31. The description of this dead end by Nicolaou et al. in his paper telling the history of the total synthesis of brevetoxin B is specially dramatic: The euphoria generated by the speed and efficiency of the sequences leading to 51 [3 in the present review] was. however, soon to dwindle, as we shall see. First, it was the miserably low-yielding conversion of the dilactone functionality into the corresponding di(thiolactone) system using Lawessons's reagents. Then the bridging reaction, attempted on the meager amount of di(thiolactone) [2 in the present review] obtained, proved equally problematic, leading to mixtures of products in low yields. In both instances, the steric hindrance of the C-13 methyl group adjacent to one of the reaction sites was to blame. That seemingly innocent methyl group, perfectly positioned to thwart our advance was almost certainly responsible for this failure. See K. C. Nicolaou Angew. Chem. 1996, 108, 644-664; Angew. Chem. Int. Ed. Engl. 1996, 35, 589-607.
32. The description of this dead end by Nicolaou et al. in his paper telling the history of the total synthesis of brevetoxin B is specially dramatic: The euphoria generated by the speed and efficiency of the sequences leading to 51 [3 in the present review] was. however, soon to dwindle, as we shall see. First, it was the miserably low-yielding conversion of the dilactone functionality into the corresponding di(thiolactone) system using Lawessons's reagents. Then the bridging reaction, attempted on the meager amount of di(thiolactone) [2 in the present review] obtained, proved equally problematic, leading to mixtures of products in low yields. In both instances, the steric hindrance of the C-13 methyl group adjacent to one of the reaction sites was to blame. That seemingly innocent methyl group, perfectly positioned to thwart our advance was almost certainly responsible for this failure. See K. C. Nicolaou Angew. Chem. 1996, 108, 644-664; Angew. Chem. Int. Ed. Engl. 1996, 35, 589-607.
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107. a) R. M. Borzilleri, S. M. Weinreb, M. Parvez, J. Am. Chem. Soc. 1995, 117, 10405-10413;
108. b) R. M. Borzilleri, S. M. Weinreb, M. Parvez, J. Am. Chem. Soc. 1994, 116, 9789-9740.
109. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
110. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
111. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
112. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
113. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
114. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
115. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
116. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
117. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
118. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
119. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
120. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
121. The following references are examples included in the original version of this review and may be useful as additional examples of dead ends and detours during the course of total synthesis: a) P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106-11112; b) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666; Angew. Chem. Int. Ed. Engl. 1996, 34, 2517-2519; c) M. Y. Chu-Moyer, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1994, 116, 11213-11228; d) G. E. Keck, S. F. McHardy, J. A. Murry, J. Am. Chem. Soc. 1995, 117, 7289-7290; e) Ch. H. Lee, M. Westling, T. Livinghouse, A. C. Williams, J. Am. Chem. Soc., 1992, 114, 4089-4095; f) C. P. Jasperse, D. P. Curran, J. Am. Chem. Soc. 1990, 112, 5601-5609; g) L. A. Paquette, T. Z. Wang, M. R. Sivik, J. Am. Chem. Soc. 1994, 116, 11323-11332; h) L. A. Paquette, L. Q. Sun, D. Friederich, P. B. Savage, J. Am. Chem. Soc. 1997, 119, 8438-8450; i) S. C. Sinha, A. Sinha, S. C. Sinha, K. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015; j) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; k) A. B. Smith III, T. A. Rano, N. Chida, G. A. Sulikowski, J. L. Wood, J. Am. Chem. Soc. 1992, 114, 8008-8022; l) J. D. White, K. M. Yager, T. Yakura, J. Am. Chem. Soc. 1994, 116, 1831-1838.
122. Hegedus first postulated the existence of this syndrome: L. S. Hegedus, Angew. Chem. 1988, 100, 1147-1161; Angew. Chem. Int. Ed. 1988, 27, 1113-1126.
123. Hegedus first postulated the existence of this syndrome: L. S. Hegedus, Angew. Chem. 1988, 100, 1147-1161; Angew. Chem. Int. Ed. 1988, 27, 1113-1126.