A chirally catalysed ene reaction in a novel formal total synthesis of the antitumor agent laulimalide

Tetrahedron Letters

Volumn 43, Issue 47, 2002, Pages 8471-8473

  Pitts, Michael R ^a   Mulzer, Johann ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

Antitumor compounds; Ene reaction; Microtubule stabilisation; Natural products; Stereoselective synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; LAULIMALIDE;

ALKYLATION; ARTICLE; CATALYST; CHIRALITY; DRUG SYNTHESIS; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 0037131756     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02086-5     Document Type: Article

References (51)

1. Quinoa E., Kakou Y., Crews P. J. Org. Chem. 53:1988;3642.
2. Corley D.G., Herb R., Moore R.E., Scheuer P.J. J. Org. Chem. 53:1988;3644.
3. Jefford C.W., Bernardinelli G., Tanaka J., Higa T. Tetrahedron Lett. 37:1996;159.
4. Mooberry S.L., Tien G., Hernandez A., Plubrukarn A., Davidson B.S. Cancer Res. 59:1999;653.
5. EU Research Network: Design and Synthesis of Novel Paclitaxel (Taxol) Mimics Using a Common Pharmacophore Model for Microtubule-Stabilising Anticancer Agents (MSAAs) HPRN-CT-2000-00018.
6. Nicolaou K.C., Roschangar F., Vourloumis D. Angew. Chem., Int. Ed. Engl. 37:1998;2014.
7. Bollag D.M., McQueney P.A., Zhu J., Hensens O., Koupal L., Liesch J., Goetz M., Lazirides E., Woods C.M. Cancer Res. 55:1995;2325.
8. Hung D.T., Chen J., Schreiber S.L. Chem. Biol. 3:1996;287.
9. ter Haar E., Kowalski R.J., Hamel E., Lin C.M., Longley R.E., Gunasekera S.P., Rosenkranz H.S., Day B.W. Biochemistry. 35:1996;243.
10. Lindel T., Jensen P.R., Fenical W., Long B.H., Casazza A.M., Carboni J., Fairchild C.R. J. Am. Chem. Soc. 119:1997;8744.
11. Mulzer J., Öhler E., Enev V.S., Hanbauer M. Adv. Synth. Catal. 344:2002;573.
12. Mulzer J., Öhler E. Angew. Chem., Int. Ed. 40:2001;3842.
13. Enev V.S., Kaehlig H., Mulzer J. J. Am. Chem. Soc. 123:2001;10764.
14. Mulzer J., Hanbauer M. Tetrahedron Lett. 43:2002;3381.
15. For other total syntheses of 1, see: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2001, 42, 3399; © Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973; (d) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 3149; (e) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956; (f) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958; (g) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841.
16. For other total syntheses of 1, see: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2001, 42, 3399; © Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973; (d) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 3149; (e) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956; (f) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958; (g) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841.
17. For other total syntheses of 1, see: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2001, 42, 3399; © Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973; (d) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 3149; (e) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956; (f) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958; (g) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841.
18. For other total syntheses of 1, see: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2001, 42, 3399; © Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973; (d) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 3149; (e) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956; (f) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958; (g) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841.
19. For other total syntheses of 1, see: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2001, 42, 3399; © Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973; (d) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 3149; (e) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956; (f) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958; (g) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841.
20. For other total syntheses of 1, see: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2001, 42, 3399; © Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973; (d) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 3149; (e) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956; (f) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958; (g) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841.
21. For other total syntheses of 1, see: (a) Ghosh, A. K.; Wang, Y. J. Am. Chem. Soc. 2000, 122, 11027; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2001, 42, 3399; © Ghosh, A. K.; Wang, Y.; Kim, J. T. J. Org. Chem. 2001, 66, 8973; (d) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 3149; (e) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956; (f) Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, 124, 5958; (g) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841.
22. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
23. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
24. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
25. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
26. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
27. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
28. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
29. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
30. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
31. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
32. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
33. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
34. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
35. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
36. For synthesis of major fragments, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427; (b) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319; © Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 4705; (d) Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011; (e) Shimizu, A.; Nishiyama, S. Synlett 1998, 1209; (f) Mulzer, J.; Hanbauer, M. Tetrahedron Lett. 2000, 41, 33; (g) Dorling, E. K., Öhler, E.; Mulzer, J. Tetrahedron Lett. 2000, 41, 6321; (h) Dorling, E. K., Öhler, E.; Mantoulidis, M.; Mulzer, J. Synlett 2001, 1105; (i) Ahmed, A.; Öhler, E.; Mulzer, J. Synthesis 2001, 2007; (j) Nadolski, G. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 797; (k) Messenger, B. T.; Davidson B. S. Tetrahedron Lett. 2001, 42, 801; (l) Sivaramakrishnan, A.; Nadolski, G. T.; McAlexander, I. A.; Davidson B. S. Tetrahedron Lett. 2002, 43, 213; (m) Paterson, I.; De Savi, C.; Tudge, M. Org. Lett. 2001, 3, 213; (n) Lee, H. W.; Jeong, C.-S.; Yoon, S. H.; Lee, I.-Y. C.; Bull. Korean Chem. Soc. 2001, 22, 791; (o) Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179.
37. Mikami K., Terada M., Narisawa S., Nakai T. Org. Synth. 71:1993;14.
38. Hilpert H. Tetrahedron. 57:2001;7675.
39. Mikami K., Terada M., Nakai T. J. Am. Chem. Soc. 111:1989;1940.
40. Mikami K., Terada M., Nakai T. J. Am. Chem. Soc. 112:1990;3949.
41. Dias L.C. Curr. Org. Chem. 4:2000;305.
42. Qian Ch., Wang L. Tetrahedron: Asymmetry. 11:2000;2347.
43. Manickam G., Sundarayan G. Tetrahedron: Asymmetry. 10:1999;2913.
44. Evans D.A., Tregay P.W., Burgey Ch.S., Paras N.A., Vojkovski T. J. Am. Chem. Soc. 122:2000;7936.
45. Jadhav P.K., Bhat K.S., Perumal T., Brown H.C. J. Org. Chem. 51:1986;432.
46. Grubbs R.H., Chang S. Tetrahedron. 54:1998;4413.
47. Armstrong S.K. J. Chem. Soc., Perkin Trans. 1. 1998;371.
48. Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012.
49. Trinka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18.
50. 2).
51. 2).