Concise total synthesis of (-)-muricatacin by tandem ring-closing/cross metathesis

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4143-4145

  Quinn, Kevin J ^a   Isaacs, André K ^a   Arvary, Rebecca A ^a  

^a Department of Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; MURICATACIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; MOLECULAR RECOGNITION; OXYGENATION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 9444286984     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol040047f     Document Type: Article

References (34)

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9. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
10. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
11. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
12. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
13. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
14. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
15. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
16. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
17. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
18. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
19. For recent syntheses of muricatacin, see: (a) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Org. Lett. 2003, 5, 2923. (c) Popsavin, V.; Krstic, I.; Popsavin, M. Tetrahedron Lett. 2003, 44, 8897. (d) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101. (e) Carda, M.; Rodriguez, S.; Gonzalez, F.; Castillo, E.; Villanueva, A.; Marco, J. A. Eur. J. Org. Chem. 2002, 15, 2649. (f) Chandrasekhar, M.; Chandra, K. L.; Singh, V. K. Tetrahedron Lett. 2002, 43, 2773. (g) Konno, H.; Hiura, N.; Yanura, M. Heterocycles 2002, 57, 1793. (h) Baylon, C.; Prestat, G.; Heck, M. P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3833. (i) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 727, 11680. (j) Solladie, G.; Hanquet, G.; Izzo, I.; Crumbie, R. Tetrahedron Lett. 1999, 40, 3071. (k) Couladouros, E. A.; Mihou, A. P. Tetrahedron Lett. 1999, 40, 4861.
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