Stereoselective synthesis and determination of the cytotoxic properties of spicigerolide and three of its stereoisomers

Journal of Organic Chemistry

Volumn 68, Issue 14, 2003, Pages 5672-5676

  Falomir, Eva ^a   Murga, Juan ^a   Ruiz, Purificación ^a   Carda, Miguel ^a   Marco, J Alberto ^b   Pereda Miranda, Rogelio ^c   Fragoso Serrano, Mabel ^c   Cerda García Rojas, Carlos M ^d  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^d DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERS; SYNTHESIS (CHEMICAL);

STEREOSELECTIVE SYNTHESIS;

AROMATIC HYDROCARBONS;

CYTOTOXIC AGENT; LACTONE; NATURAL PRODUCT; RHAMNOSE; SPICIGEROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CHIRALITY; COLON CARCINOMA; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NASOPHARYNX CANCER; OVARY CANCER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; THIN LAYER CHROMATOGRAPHY; UTERINE CERVIX CANCER;

ANTINEOPLASTIC AGENTS; CELL DEATH; CELL LINE, TUMOR; CYCLIZATION; HUMANS; LACTONES; ORGAN SPECIFICITY; RHAMNOSE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037662050     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034470y     Document Type: Article

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34. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
35. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
36. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
37. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
38. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
39. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
40. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
41. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
42. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
43. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
44. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
45. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
46. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
47. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
48. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
49. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.
50. RCM reactions have often been used in the course of the synthesis of natural products containing lactone rings. For recent examples, see: Argentilactone: Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. Boronolide: Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. Epotilones: Nicolaou, K. C.; Ritzén, A.; Namoto, K. Chem. Commun. 2001, 1523-1535. Fostriecin: Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618. Fuji, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736. Goniodiol: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550. Banwell, M. G.; Coster, M. J.; Karunaratne, O. P.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 1622-1624. Goniothalamin: Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586. Laulimalide: Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973-8982. Malyngolide: Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929-8936. Phorboxazoles: Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009-6018. Peloruside A: Ghosh, A. K.; Kim, J.-H. Tetrahedron Lett. 2003, 44, 3967-3969. Strictifolione: Tosaki, S.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495-498. Tetrahydrolipstatin: Ghosh, A. K.; Liu, C. Chem. Commun. 1999, 1743-1744. Umuravumbolide: Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20. Zearalenone: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995. See also ref 12.