Stereoconvergent transformation of 1,2a-disubstituted benzo[b]cyclobuta[d] pyrans to 1,3-disubstituted tetrahydrodibenzofuran-4-ols and its application to the second-generation synthesis of (±)-linderol A

Synlett

Volumn , Issue 11, 2004, Pages 1897-1900

  Yamashita, Masayuki ^a   Inaba, Tomoki ^a   Shimizu, Takashi ^a   Kawasaki, Ikuo ^a   Ohta, Shunsaku ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Fused ring systems; Linderol A; Photochemistry; Stereoconvergent reaction; Ylides

Indexed keywords

ALCOHOL DERIVATIVE; COUMARIN DERIVATIVE; CYCLOBUTANE; DIMETHYLSULFOXONIUM METHYLIDE; FURAN DERIVATIVE; LINDEROL A; MELANIN; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; BIOTRANSFORMATION; CYCLOADDITION; NUCLEAR OVERHAUSER EFFECT; PHOTOCHEMISTRY; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 4544295155     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-830875     Document Type: Article

References (39)

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9. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
10. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
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12. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
13. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
14. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
15. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
16. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
17. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
18. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
19. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
20. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
21. Recent reviews: (a) Dolbier, W. R. Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (b) Fedoryski, M. Chem. Rev. 2003, 103, 1099. (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133. (d) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (e) Baldwin, J. E. Chem. Rev. 2003, 103, 1197. (f) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213. (g) Baird, M. Chem. Rev. 2003, 103, 1271. (h) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (i) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449. (j) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485. (k) Donaldson, W. A. Tetrahedron 2001, 57, 8589. (1) Sydnes, L. K. Eur. J. Org. Chem. 2000, 3511. (m) Iwasawa, N.; Narasaka, K. Top. Curr. Chem. 2000, 207, 69. (n) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89. (o) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149. (p) Nemoto, H.; Fukumoto, K. Synlett 1997, 863. (q) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1.
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