Effects of allylic and homoallylic substituents on the ring closing metathesis reaction used to synthesise simplified eleuthesides

Tetrahedron Letters

Volumn 44, Issue 43, 2003, Pages 7913-7919

  Caggiano, Lorenzo ^a   Castoldi, Damiano ^a   Beumer, Raphael ^a,b   Bayón, Pau ^a,c   Telser, Joachim ^a,d   Gennari, Cesare ^a  

^a CNR   (Italy)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^d BAYER AG   (Germany)

Author keywords

Antitumour compounds; P methoxyphenyl (PMP); Protective groups; Ring closing metathesis

Indexed keywords

ALCOHOL DERIVATIVE; ANTINEOPLASTIC AGENT; ELEUTHEROBIN; PHENYL GROUP; SARCODICTYIN A; SARCODICTYIN B; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; RING CLOSING METATHESIS;

EID: 0141760258     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.010     Document Type: Article

References (43)

1. For a comprehensive review on the chemistry and biology of the eleuthesides, see: Nicolaou, K. C.; Pfefferkorn, J.; Xu, J.; Winssinger, N.; Ohshima, T.; Kim, S.; Hosokawa, S.; Vourloumis, D.; van Delft, F.; Li, T. Chem. Pharm. Bull. 1999, 47, 1199 and references therein. See also: Britton, R.; de Silva, E. D.; Bigg, C. M.; McHardy, L. M.; Roberge, M.; Andersen, R. J. J. Am. Chem. Soc. 2001, 123, 8632.
2. For a comprehensive review on the chemistry and biology of the eleuthesides, see: Nicolaou, K. C.; Pfefferkorn, J.; Xu, J.; Winssinger, N.; Ohshima, T.; Kim, S.; Hosokawa, S.; Vourloumis, D.; van Delft, F.; Li, T. Chem. Pharm. Bull. 1999, 47, 1199 and references therein. See also: Britton, R.; de Silva, E. D.; Bigg, C. M.; McHardy, L. M.; Roberge, M.; Andersen, R. J. J. Am. Chem. Soc. 2001, 123, 8632.
3. Total syntheses of the eleuthesides have been accomplished by the Nicolaou and Danishefsky groups, see: (a) Nicolaou, K. C.; Xu, J. Y.; Kim, S.; Pfefferkorn, J.; Ohshima, T.; Vourloumis, D.; Hosokawa, S. J. Am. Chem. Soc. 1998, 120, 8661; (b) Nicolaou, K. C.; Ohshima, T.; Hosokawa, S.; van Delft, F. L.; Vourloumis, D.; Xu, J. Y.; Pfefferkorn, J.; Kim, S. J. Am. Chem. Soc. 1998, 120, 8674; (c) Chen, X.-T.; Bhattacharya, S. K.; Zhou, B.; Gutteridge, C. E.; Pettus, T. R. R.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 6563.
4. Total syntheses of the eleuthesides have been accomplished by the Nicolaou and Danishefsky groups, see: (a) Nicolaou, K. C.; Xu, J. Y.; Kim, S.; Pfefferkorn, J.; Ohshima, T.; Vourloumis, D.; Hosokawa, S. J. Am. Chem. Soc. 1998, 120, 8661; (b) Nicolaou, K. C.; Ohshima, T.; Hosokawa, S.; van Delft, F. L.; Vourloumis, D.; Xu, J. Y.; Pfefferkorn, J.; Kim, S. J. Am. Chem. Soc. 1998, 120, 8674; (c) Chen, X.-T.; Bhattacharya, S. K.; Zhou, B.; Gutteridge, C. E.; Pettus, T. R. R.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 6563.
5. Total syntheses of the eleuthesides have been accomplished by the Nicolaou and Danishefsky groups, see: (a) Nicolaou, K. C.; Xu, J. Y.; Kim, S.; Pfefferkorn, J.; Ohshima, T.; Vourloumis, D.; Hosokawa, S. J. Am. Chem. Soc. 1998, 120, 8661; (b) Nicolaou, K. C.; Ohshima, T.; Hosokawa, S.; van Delft, F. L.; Vourloumis, D.; Xu, J. Y.; Pfefferkorn, J.; Kim, S. J. Am. Chem. Soc. 1998, 120, 8674; (c) Chen, X.-T.; Bhattacharya, S. K.; Zhou, B.; Gutteridge, C. E.; Pettus, T. R. R.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 6563.
6. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
7. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
8. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
9. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
10. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
11. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
12. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
13. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
14. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
15. Partial syntheses of the eleuthesides have also been described, see: (a) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153; (b) Baron, A.; Caprio, V.; Mann, J. Tetrahedron Lett. 1999, 40, 9321; (c) Carter, R.; Hodgetts, K.; McKenna, J.; Magnus, P.; Wren, S. Tetrahedron 2000, 56, 4367; (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254; (e) Xu, Q.; Weeresakare, M.; Rainier, J. D. Tetrahedron 2001, 57, 8029; (f) Ceccarelli, S.; Piarulli, U.; Telser, J.; Gennari, C. Tetrahedron Lett. 2001, 42, 7421; (g) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron 2001, 57, 8531; (h) Sandoval, C.; Redero, E.; Mateos-Timoneda, M. A.; Bermejo, F. A. Tetrahedron Lett. 2002, 43, 6521; (i) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379; (j) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805; (k) Scalabrino, G.; Sun, X.-W.; Mann, J.; Baron, A. Org. Biomol. Chem. 2003, 1, 318.
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25. % Yields reported in brackets are calculated considering the recovered starting material. Cy=cyclohexyl; Mes=mesityl; TBDPS=tert-butyldiphenylsilyl; PMB=p-methoxybenzyl; Piv=t-BuCO; Bz=PhCO; MOM=methoxymethyl; DMAP=4-dimethylaminopyridine; CAN=cerium(IV) ammonium nitrate; PMP=p-methoxyphenyl; rt=room temperature.
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34. The use of 'second generation' metathesis catalysts results in the selective formation of the thermodynamically favored stereoisomeric products in RCM reactions furnishing medium-sized rings, see: (a) Lee, C. W.; Grubbs. R. H. Org. Lett. 2000, 2, 2145; (b) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061; (c) Murga, J.; Falomir, E.; Garcìa-Fortanet, J.; Carda, M.; Marco, J. A. Org. Lett. 2002, 4, 3447; (d) Prunet, J. Angew. Chem. Int. Ed. 2003, 42, 2826.
35. The use of 'second generation' metathesis catalysts results in the selective formation of the thermodynamically favored stereoisomeric products in RCM reactions furnishing medium-sized rings, see: (a) Lee, C. W.; Grubbs. R. H. Org. Lett. 2000, 2, 2145; (b) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061; (c) Murga, J.; Falomir, E.; Garcìa-Fortanet, J.; Carda, M.; Marco, J. A. Org. Lett. 2002, 4, 3447; (d) Prunet, J. Angew. Chem. Int. Ed. 2003, 42, 2826.
36. The use of 'second generation' metathesis catalysts results in the selective formation of the thermodynamically favored stereoisomeric products in RCM reactions furnishing medium-sized rings, see: (a) Lee, C. W.; Grubbs. R. H. Org. Lett. 2000, 2, 2145; (b) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061; (c) Murga, J.; Falomir, E.; Garcìa-Fortanet, J.; Carda, M.; Marco, J. A. Org. Lett. 2002, 4, 3447; (d) Prunet, J. Angew. Chem. Int. Ed. 2003, 42, 2826.
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39. For discussions on the role of allylic oxygen substituents in the RCM reaction, see: (a) White, J. D.; Hrnciar, P. J. Org. Chem. 2000, 65, 9129; (b) Paquette, L. A.; Efremov, I. J. Am. Chem. Soc. 2001, 123, 4492; (c) Maishal, T. K.; Sinha-Mahapatra, D. K.; Paranjape, K.; Sarkar, A. Tetrahedron Lett. 2002, 43, 2263.
40. For discussions on the role of allylic oxygen substituents in the RCM reaction, see: (a) White, J. D.; Hrnciar, P. J. Org. Chem. 2000, 65, 9129; (b) Paquette, L. A.; Efremov, I. J. Am. Chem. Soc. 2001, 123, 4492; (c) Maishal, T. K.; Sinha-Mahapatra, D. K.; Paranjape, K.; Sarkar, A. Tetrahedron Lett. 2002, 43, 2263.
41. Successful RCM reactions have been reported with an acetonide protecting allylic and homoallyic alcohols, see Ref. 11c.
42. For the effect of the stereochemistry of the homoallylic and allylic substituents on the RCM performance in the formation of seven- and eight-membered rings, see: Krafft M. E., Cheung Y.Y., Kerrigan S.A., Abboud K.A. Tetrahedron Lett. 44:2003;839.
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