Cationic cyclopentannelation of allene ethers

Accounts of Chemical Research

Volumn 36, Issue 4, 2003, Pages 284-290

  Tius, Marcus A ^a,b  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF HAWAII CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; AMIDE; CATION; ETHER DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLOPENTANNELATION; ENANTIOSELECTIVITY; PRECURSOR;

ALLYL COMPOUNDS; AMIDES; CATIONS; CYCLIZATION; CYCLOPENTANES; ETHERS; STEREOISOMERISM;

EID: 0037395377     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0200394     Document Type: Article

References (38)

1. Tius, M. A.; Astrab, D. P. A Cationic Cyclopentannelation. Tetrahedron Lett. 1984, 25, 1539-1542.
2. This begs the question: "What happens to 1 if the m-CPBA is buffered?" For the answer, the reader is directed to: Tius, M. A.; Cullingham, J. M.; Ali, S. Hydroxyquinone Annelation. J. Chem. Soc., Chem. Commun. 1989, 867-869.
3. Tius, M. A.; Trehan, S. A Concise Synthesis of D,L-Methylenomycin A and D,L-epi-Methylenomycin A. J. Org. Chem. 1989, 54, 46-51.
4. Interesting related work has been reported by others: (a) Browder, C. C.; Marmsaeter, F. P.; West, F. G. Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes. Org. Lett. 2001, 3, 3033-3035. (b) Giese, S.; West, F. G. Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization. Tetrahedron 2000, 56, 10221-10228. (c) Bender, J. A.; Arif, A. M.; West, F. G. Nazarov-Initiated Diastereoselective Cascade Polycyclization of Aryltrienones. J. Am. Chem. Soc. 1999, 121, 7443-7444. (d) Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones. Tetrahedron Lett. 1998, 39, 7491-7494. (e) Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogues of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis. J. Org. Chem. 1994, 59, 5292-5304. (f) Jacobi, P. A.; Cann, R. O.; Skibbie, D. F. A Convenient Synthesis of Methylenomycin B. Further Mechanistic Studies on the SET Catalyzed Electrocyclization of Enynones. Tetrahedron Lett. 1992, 33, 2265-2268. (g) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. Silicon-Directed Nazarov Cyclizations. 8. Stereoelectronic Control of Torquoselectivity. J. Org. Chem. 1990, 55, 5543-5545. (h) Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Enynones in Organic Synthesis. I. Spiroannulation by Tandem oxy-Cope Rearrangement-Electrocyclic Ring Closure. Tetrahedron Lett. 1988, 29, 6865-6868, et seq.
5. Interesting related work has been reported by others: (a) Browder, C. C.; Marmsaeter, F. P.; West, F. G. Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes. Org. Lett. 2001, 3, 3033-3035. (b) Giese, S.; West, F. G. Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization. Tetrahedron 2000, 56, 10221-10228. (c) Bender, J. A.; Arif, A. M.; West, F. G. Nazarov-Initiated Diastereoselective Cascade Polycyclization of Aryltrienones. J. Am. Chem. Soc. 1999, 121, 7443-7444. (d) Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones. Tetrahedron Lett. 1998, 39, 7491-7494. (e) Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogues of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis. J. Org. Chem. 1994, 59, 5292-5304. (f) Jacobi, P. A.; Cann, R. O.; Skibbie, D. F. A Convenient Synthesis of Methylenomycin B. Further Mechanistic Studies on the SET Catalyzed Electrocyclization of Enynones. Tetrahedron Lett. 1992, 33, 2265-2268. (g) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. Silicon-Directed Nazarov Cyclizations. 8. Stereoelectronic Control of Torquoselectivity. J. Org. Chem. 1990, 55, 5543-5545. (h) Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Enynones in Organic Synthesis. I. Spiroannulation by Tandem oxy-Cope Rearrangement-Electrocyclic Ring Closure. Tetrahedron Lett. 1988, 29, 6865-6868, et seq.
6. Interesting related work has been reported by others: (a) Browder, C. C.; Marmsaeter, F. P.; West, F. G. Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes. Org. Lett. 2001, 3, 3033-3035. (b) Giese, S.; West, F. G. Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization. Tetrahedron 2000, 56, 10221-10228. (c) Bender, J. A.; Arif, A. M.; West, F. G. Nazarov-Initiated Diastereoselective Cascade Polycyclization of Aryltrienones. J. Am. Chem. Soc. 1999, 121, 7443-7444. (d) Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones. Tetrahedron Lett. 1998, 39, 7491-7494. (e) Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogues of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis. J. Org. Chem. 1994, 59, 5292-5304. (f) Jacobi, P. A.; Cann, R. O.; Skibbie, D. F. A Convenient Synthesis of Methylenomycin B. Further Mechanistic Studies on the SET Catalyzed Electrocyclization of Enynones. Tetrahedron Lett. 1992, 33, 2265-2268. (g) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. Silicon-Directed Nazarov Cyclizations. 8. Stereoelectronic Control of Torquoselectivity. J. Org. Chem. 1990, 55, 5543-5545. (h) Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Enynones in Organic Synthesis. I. Spiroannulation by Tandem oxy-Cope Rearrangement-Electrocyclic Ring Closure. Tetrahedron Lett. 1988, 29, 6865-6868, et seq.
7. Interesting related work has been reported by others: (a) Browder, C. C.; Marmsaeter, F. P.; West, F. G. Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes. Org. Lett. 2001, 3, 3033-3035. (b) Giese, S.; West, F. G. Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization. Tetrahedron 2000, 56, 10221-10228. (c) Bender, J. A.; Arif, A. M.; West, F. G. Nazarov-Initiated Diastereoselective Cascade Polycyclization of Aryltrienones. J. Am. Chem. Soc. 1999, 121, 7443-7444. (d) Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones. Tetrahedron Lett. 1998, 39, 7491-7494. (e) Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogues of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis. J. Org. Chem. 1994, 59, 5292-5304. (f) Jacobi, P. A.; Cann, R. O.; Skibbie, D. F. A Convenient Synthesis of Methylenomycin B. Further Mechanistic Studies on the SET Catalyzed Electrocyclization of Enynones. Tetrahedron Lett. 1992, 33, 2265-2268. (g) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. Silicon-Directed Nazarov Cyclizations. 8. Stereoelectronic Control of Torquoselectivity. J. Org. Chem. 1990, 55, 5543-5545. (h) Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Enynones in Organic Synthesis. I. Spiroannulation by Tandem oxy-Cope Rearrangement-Electrocyclic Ring Closure. Tetrahedron Lett. 1988, 29, 6865-6868, et seq.
8. Interesting related work has been reported by others: (a) Browder, C. C.; Marmsaeter, F. P.; West, F. G. Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes. Org. Lett. 2001, 3, 3033-3035. (b) Giese, S.; West, F. G. Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization. Tetrahedron 2000, 56, 10221-10228. (c) Bender, J. A.; Arif, A. M.; West, F. G. Nazarov-Initiated Diastereoselective Cascade Polycyclization of Aryltrienones. J. Am. Chem. Soc. 1999, 121, 7443-7444. (d) Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones. Tetrahedron Lett. 1998, 39, 7491-7494. (e) Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogues of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis. J. Org. Chem. 1994, 59, 5292-5304. (f) Jacobi, P. A.; Cann, R. O.; Skibbie, D. F. A Convenient Synthesis of Methylenomycin B. Further Mechanistic Studies on the SET Catalyzed Electrocyclization of Enynones. Tetrahedron Lett. 1992, 33, 2265-2268. (g) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. Silicon-Directed Nazarov Cyclizations. 8. Stereoelectronic Control of Torquoselectivity. J. Org. Chem. 1990, 55, 5543-5545. (h) Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Enynones in Organic Synthesis. I. Spiroannulation by Tandem oxy-Cope Rearrangement-Electrocyclic Ring Closure. Tetrahedron Lett. 1988, 29, 6865-6868, et seq.
9. Interesting related work has been reported by others: (a) Browder, C. C.; Marmsaeter, F. P.; West, F. G. Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes. Org. Lett. 2001, 3, 3033-3035. (b) Giese, S.; West, F. G. Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization. Tetrahedron 2000, 56, 10221-10228. (c) Bender, J. A.; Arif, A. M.; West, F. G. Nazarov-Initiated Diastereoselective Cascade Polycyclization of Aryltrienones. J. Am. Chem. Soc. 1999, 121, 7443-7444. (d) Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones. Tetrahedron Lett. 1998, 39, 7491-7494. (e) Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogues of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis. J. Org. Chem. 1994, 59, 5292-5304. (f) Jacobi, P. A.; Cann, R. O.; Skibbie, D. F. A Convenient Synthesis of Methylenomycin B. Further Mechanistic Studies on the SET Catalyzed Electrocyclization of Enynones. Tetrahedron Lett. 1992, 33, 2265-2268. (g) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. Silicon-Directed Nazarov Cyclizations. 8. Stereoelectronic Control of Torquoselectivity. J. Org. Chem. 1990, 55, 5543-5545. (h) Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Enynones in Organic Synthesis. I. Spiroannulation by Tandem oxy-Cope Rearrangement-Electrocyclic Ring Closure. Tetrahedron Lett. 1988, 29, 6865-6868, et seq.
10. Interesting related work has been reported by others: (a) Browder, C. C.; Marmsaeter, F. P.; West, F. G. Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes. Org. Lett. 2001, 3, 3033-3035. (b) Giese, S.; West, F. G. Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization. Tetrahedron 2000, 56, 10221-10228. (c) Bender, J. A.; Arif, A. M.; West, F. G. Nazarov-Initiated Diastereoselective Cascade Polycyclization of Aryltrienones. J. Am. Chem. Soc. 1999, 121, 7443-7444. (d) Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones. Tetrahedron Lett. 1998, 39, 7491-7494. (e) Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogues of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis. J. Org. Chem. 1994, 59, 5292-5304. (f) Jacobi, P. A.; Cann, R. O.; Skibbie, D. F. A Convenient Synthesis of Methylenomycin B. Further Mechanistic Studies on the SET Catalyzed Electrocyclization of Enynones. Tetrahedron Lett. 1992, 33, 2265-2268. (g) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. Silicon-Directed Nazarov Cyclizations. 8. Stereoelectronic Control of Torquoselectivity. J. Org. Chem. 1990, 55, 5543-5545. (h) Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Enynones in Organic Synthesis. I. Spiroannulation by Tandem oxy-Cope Rearrangement-Electrocyclic Ring Closure. Tetrahedron Lett. 1988, 29, 6865-6868, et seq.
11. Interesting related work has been reported by others: (a) Browder, C. C.; Marmsaeter, F. P.; West, F. G. Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes. Org. Lett. 2001, 3, 3033-3035. (b) Giese, S.; West, F. G. Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization. Tetrahedron 2000, 56, 10221-10228. (c) Bender, J. A.; Arif, A. M.; West, F. G. Nazarov-Initiated Diastereoselective Cascade Polycyclization of Aryltrienones. J. Am. Chem. Soc. 1999, 121, 7443-7444. (d) Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones. Tetrahedron Lett. 1998, 39, 7491-7494. (e) Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogues of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis. J. Org. Chem. 1994, 59, 5292-5304. (f) Jacobi, P. A.; Cann, R. O.; Skibbie, D. F. A Convenient Synthesis of Methylenomycin B. Further Mechanistic Studies on the SET Catalyzed Electrocyclization of Enynones. Tetrahedron Lett. 1992, 33, 2265-2268. (g) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. Silicon-Directed Nazarov Cyclizations. 8. Stereoelectronic Control of Torquoselectivity. J. Org. Chem. 1990, 55, 5543-5545. (h) Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Enynones in Organic Synthesis. I. Spiroannulation by Tandem oxy-Cope Rearrangement-Electrocyclic Ring Closure. Tetrahedron Lett. 1988, 29, 6865-6868, et seq.
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