Correction to: Synthesis of seven-membered ring glycals via endo-selective alkynol cycloisomerization (Organic Letters (2004) 6:21 (3877-3880) DOI: 10.1021/ol0483495);Synthesis of seven-membered ring glycals via endo-selective alkynol cycloisomerization

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3877-3880

  Alcázar, Eva ^a,b   Pletcher, Joseph M ^a   McDonald, Frank E ^a  

^a EMORY UNIVERSITY   (United States)

^b Process Development   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ALKYL GROUP; TUNGSTEN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ISOMERIZATION; PHASE TRANSITION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 7044241203     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.9b01022     Document Type: Erratum

References (48)

1. (a) McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103.
2. (b) McDonald, F. E.; Reddy, K. R.; Díaz, Y. J. Am. Chem. Soc. 2000, 122, 4304.
3. McDonald, F. E.; Reddy, K. R. J. Organomet. Chem. 2001, 617-618, 444.
4. (a) Chisholm, M. H.; Clark, H. C. Acc. Chem. Res. 1973, 6, 202.
5. (b) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59.
6. (a) McDonald, F. E.; Reddy, K. S. Angew. Chem., Int. Ed. 2001, 40, 3653.
7. (b) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
8. McDonald, F. E.; Wu, M. Org. Lett. 2002, 4, 3979.
9. Davidson, M. H.; McDonald, F. E. Org. Lett. 2004, 6, 1601.
10. (a) Jiang, S.; Singh, G.; Batsanov, A. S. Tetrahedron: Asymmetry 2000, 11, 3873.
11. (b) Hughes, N. A.; Speakman, P. R. H. Carbohydr. Res. 1965, 1, 171.
12. Mella, M.; Panza, L.; Ronchetti, F.; Toma, L. Tetrahedron 1988, 44, 1673.
13. Thiéry, J.-C.; Fréchou, C.; Demailly, G. Tetrahedron Lett. 2000, 41, 6337.
14. See Supporting Information for substrate syntheses, cycloisomerization conditions, and detailed product characterization.
15. (a) Stevens, J. D. J. Chem. Soc., Chem. Commun. 1969, 1140.
16. (b) Ng, C. J.; Stevens, J. D. Carbohydr. Res. 1996, 284, 241.
17. (a) Anet, E. F. L. J. Carbohydr. Res. 1968, 8, 164.
18. (b) Grindley, T. B.; Gulasekharan, V. J. Chem. Soc., Chem. Commun. 1978, 1073.
19. (a) Micheel, F.; Suckfüll, F. Ann. 1933, 502, 85.
20. (b) Ward, D. E.; Liu, Y.; Rhee, C. K. Can. J. Chem. 1994, 72, 1429.
21. McAuliffe, J. C.; Hindsgaul, O. Synlett 1998, 307.
22. Contour, M.-O.; Fayet, C.; Gelas, J. Carbohydr. Res. 1990, 201, 150.
23. For formation of septanose glycals via ring-closing metathesis of alkenes tethered to O-vinyl ethers, see: (a) Peczuh, M. W.; Snyder, N. L. Tetrahedron Lett. 2003, 44, 4057. (b) Peczuh, M. W.; Snyder, N. L.; Fyvie, W. S. Carbohydr. Res. 2004, 339, 1163.
24. For formation of septanose glycals via ring-closing metathesis of alkenes tethered to O-vinyl ethers, see: (a) Peczuh, M. W.; Snyder, N. L. Tetrahedron Lett. 2003, 44, 4057. (b) Peczuh, M. W.; Snyder, N. L.; Fyvie, W. S. Carbohydr. Res. 2004, 339, 1163.
25. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
26. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
27. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
28. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
29. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
30. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
31. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
32. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
33. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
34. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
35. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
36. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
37. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
38. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
39. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
40. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
41. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
42. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
43. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
44. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
45. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
46. For representative other methods for formation of oxepins via: ring-closing metathesis-isomerization: (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (b) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390. (d) Schmidt, B. Eur. J. Org. Chem. 2003, 816. Oxidation-dehydration of 1,6-hexanediol: (e) Larkin, D. R. J. Org. Chem. 1965, 30, 335. (f) Oakes, F. T.; Yang, F.-A.; Sebastian, J. F. J. Org. Chem. 1982, 47, 3094. Via lactone enol phosphate or triflates: (g) Kane, V. V.; Doyle, D. L.; Ostrowski, P. G. Tetrahedron Lett. 1980, 21, 2643. (h) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313. (i) Nicolaou, K. C. J. Am. Chem. Soc. 1997, 119, 5469. Via anionic cyclization of allyl glycidyl ether: (j) Ichikawa, Y.; Niitsuma, S.; Kato, K.; Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625. (k) Bird, C. W.; Hormozi, N. Tetrahedron Lett. 1990, 31, 3501. Oxidative expansion with peroxides: (1) Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459. (m) Goodman, R. M.; Kishi, Y. J. Org. Chem. 1994, 59, 5125. [3.3]-Rearrangements: (n) Wenkert, E.; Greenberg, R. S.; Kim, H. S. Helv. Chim. Acta 1987, 70, 2159. (o) Clark, D. L.; Chou, W.-N.; White, J. B. J. Org. Chem. 1990, 55, 3975. (p) Sugiyama, J.; Tanikawa, K.; Okada, T.; Noguchi, K.; Ueda, M.; Endo, T. Tetrahedron Lett. 1994, 35, 3111. (q) Hofmann, B.; Reissig, H.-U. Chem. Ber. 1994, 127, 2337. Conjugate oxacyclization of sulfonylallenes: (r) Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385. Cyclization of hydroxyl-terminated O-vinyl ethers: (s) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1992, 48, 3991. Intramolecular nucleophilic condensation with ester: (t) Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron Lett. 1991, 32, 6947. (u) Rahim, M. A.; Fujiwara, T.; Takeda, T. Tetrahedron 2000, 56, 763. Ruthenium-catalyzed cycloisomerization of α-ω-alkynoic acids: (v) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Moreno-Dorado, F. J.; Guerra, F. M.; Massanet, G. M. Chem. Commun. 2001, 2324.
47. In addition, the glycal form of the seven-membered ring sugar products provides considerable potential for stereo- and regioselective introduction of functional groups across the glycal alkene. (a) Micheel, F.; Suckfüll, F. Ann. 1933, 507, 138. (b) Refs 10c and 12b.
48. In addition, the glycal form of the seven-membered ring sugar products provides considerable potential for stereo- and regioselective introduction of functional groups across the glycal alkene. (a) Micheel, F.; Suckfüll, F. Ann. 1933, 507, 138. (b) Refs 10c and 12b.