Stereoselective Intramolecular Nicholas Reaction Using Epoxides as Nucleophiles

Organic Letters

Volumn 6, Issue 4, 2004, Pages 565-568

  Crisóstomo, Fernando R P ^a   Martín, Tomás ^a   Martín, Víctor S ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBONIC ACID DERIVATIVE; CATION; EPOXIDE; ETHER DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; OXEPANE DERIVATIVE; TERT BUTYLCARBONIC ACID DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY;

EID: 10744226244     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0363570     Document Type: Article

References (43)

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3. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
4. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
5. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
6. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
7. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
8. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
9. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
10. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
11. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
12. Representative examples of marine ladder toxins: (a) (brevetoxin-B): Lin, Y.-Y.; Risk, M.; Ray, S. M., Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc, 1981, 103, 6773-6775. (b) (brevetoxin-A): Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc, 1986, 108, 514-515. (c) (hemibrevetoxin-B): Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc., 1989, 111, 6476-6477. (d) (ciguatoxin): Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) (gambieric acids): Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem., 1992, 57, 5448-5453. (f) (gambierol): Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) (prymnesin-2): Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) (scaritoxin): Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105. (i) (yessotoxin): Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) (adriatoxin): Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
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34. 5: C, 59.99; H, 6.71. Found: C, 59.98; H, 7.19.
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36. For the influence of temperature to control the stereochemistry in cobalt induced cyclizations, see: (a) Liu, T.-Z.; Isobe, M. Tetrahedron 2000, 56, 5391-5404. (b) Takase, M.; Morikawa, T.; Abe, H.; Inouye, M. Org. Lett. 2003, 5, 625-628. (c) Reference 10b.
37. For the influence of temperature to control the stereochemistry in cobalt induced cyclizations, see: (a) Liu, T.-Z.; Isobe, M. Tetrahedron 2000, 56, 5391-5404. (b) Takase, M.; Morikawa, T.; Abe, H.; Inouye, M. Org. Lett. 2003, 5, 625-628. (c) Reference 10b.
38. For the use of electronically enriched carbonyl derivatives in cyclization reactions using 2,3-epoxy alcohols, see ref 11c.
39. Obtained by a similar sequence to that shown in Scheme 1 using a methyl ether as the protecting group at the secondary carbinol.
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43. To clarify the scheme the enantiomers of reactants and products were drawn.