Palladium-catalyzed intramolecular allylic alkylation reaction in marine natural product synthesis: Enantioselective synthesis of (+)-methyl pederate, a key intermediate in syntheses of mycalamides

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5895-5902

  Toyota, Masahiro ^a   Hirota, Masako ^a   Nishikawa, Youichi ^a   Fukumoto, Keiichiro ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METHYL PEDERATE; MYCALAMIDE A; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOCHEMISTRY; SYNTHESIS;

EID: 0032555430     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9805246     Document Type: Article

References (37)

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6. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
7. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
8. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
9. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
10. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
11. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
12. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
13. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
14. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
15. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
16. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
17. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
18. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
19. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
20. Total syntheses of mycalamides A and B and onnamide A: (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242-4245. (b) Idem J. Am. Chem. Soc. 1991, 113, 9693-9694. (c) Nakata, T.; Matsukura, H.; Jian, D.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229-8232. Related synthetic studies: (d) Tsuzuki, K.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1976, 4745-4748. (e) Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364-5370. (f) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461-6464. (g) Nakata, T.; Nagao, S.; Oishi, T. Ibid. 1985, 26, 6465-6468. (h) Matsuda, F.; Tomiyoshi, N.; Yanagiya, M.; Mastumoto, T. Tetrahedron 1988, 44, 7063-7080. (i) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191-1200. (j) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421-5424. (k) Hoffmann, R. W.; Schlapbach, A. Ibid. 1993, 34, 7903-7906. (l) Marron, T. G.; Roush, W. R. Ibid. 1995, 36, 1581-1584. (m) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346-352. (n) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc., Perkin Trans. 1 1996, 1797-1808. (o) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474-478.
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