Efficient convergent synthesis of a trans-fused 6-6-6-6-membered tetracyclic ether ring system

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 903-906

  Matsuo, Goh ^a   Hinou, Hiroshi ^a   Koshino, Hiroyuki ^a   Suenaga, Toshiro ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Acetals; Alkynes; Coupling reactions; Polyethers; Reduction; Tetrahydropyrans

Indexed keywords

1,2 DICARBONYL DERIVATIVE; ACETAL DERIVATIVE; ACETIC ACID DERIVATIVE; ALKYNE; POLYETHER DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034606975     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02173-5     Document Type: Article

References (22)

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2. For reviews, see: (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897. (b) Shimizu, Y. Chem. Rev. 1993, 93, 1685. (c) Scheuer, P. J. Tetrahedron 1994, 50, 3.
3. For reviews, see: (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897. (b) Shimizu, Y. Chem. Rev. 1993, 93, 1685. (c) Scheuer, P. J. Tetrahedron 1994, 50, 3.
4. For convergent syntheses of polycyclic tetrahydropyrans: (a) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFees, S. A.; Coulodouros, E. A.; Abe, Y.; Carrol, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (b) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (c) Alvarez, E.; Perez, R.; Rico, M.; Rodriguez, R. M.; Matrin, J. D. J. Org. Chem. 1996, 61, 3003. (d) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (e) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037. (f) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063. (g) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
5. For convergent syntheses of polycyclic tetrahydropyrans: (a) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFees, S. A.; Coulodouros, E. A.; Abe, Y.; Carrol, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (b) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (c) Alvarez, E.; Perez, R.; Rico, M.; Rodriguez, R. M.; Matrin, J. D. J. Org. Chem. 1996, 61, 3003. (d) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (e) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037. (f) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063. (g) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
6. For convergent syntheses of polycyclic tetrahydropyrans: (a) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFees, S. A.; Coulodouros, E. A.; Abe, Y.; Carrol, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (b) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (c) Alvarez, E.; Perez, R.; Rico, M.; Rodriguez, R. M.; Matrin, J. D. J. Org. Chem. 1996, 61, 3003. (d) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (e) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037. (f) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063. (g) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
7. For convergent syntheses of polycyclic tetrahydropyrans: (a) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFees, S. A.; Coulodouros, E. A.; Abe, Y.; Carrol, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (b) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (c) Alvarez, E.; Perez, R.; Rico, M.; Rodriguez, R. M.; Matrin, J. D. J. Org. Chem. 1996, 61, 3003. (d) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (e) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037. (f) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063. (g) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
8. For convergent syntheses of polycyclic tetrahydropyrans: (a) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFees, S. A.; Coulodouros, E. A.; Abe, Y.; Carrol, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (b) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (c) Alvarez, E.; Perez, R.; Rico, M.; Rodriguez, R. M.; Matrin, J. D. J. Org. Chem. 1996, 61, 3003. (d) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (e) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037. (f) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063. (g) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
9. For convergent syntheses of polycyclic tetrahydropyrans: (a) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFees, S. A.; Coulodouros, E. A.; Abe, Y.; Carrol, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (b) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (c) Alvarez, E.; Perez, R.; Rico, M.; Rodriguez, R. M.; Matrin, J. D. J. Org. Chem. 1996, 61, 3003. (d) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (e) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037. (f) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063. (g) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
10. For convergent syntheses of polycyclic tetrahydropyrans: (a) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFees, S. A.; Coulodouros, E. A.; Abe, Y.; Carrol, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (b) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (c) Alvarez, E.; Perez, R.; Rico, M.; Rodriguez, R. M.; Matrin, J. D. J. Org. Chem. 1996, 61, 3003. (d) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (e) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037. (f) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063. (g) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
11. During the course of our present study, the same strategy was reported by the Murai-Fujiwara group at the 77th National Meeting of the Chemical Society of Japan, on Sept. 18 at Sapporo. T.N. thanks Prof. A. Murai (Hokkaido University) for generously providing their manuscript, submitted to Tetrahedron Lett. Thus, we now disclose our recent results in this paper.
12. The most stable conformers of v (R=Me) and vi (R=Me), indicated by MM2*/MacroModel 6.0 calculations (Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440), were used for PM3/MOPAC.
13. 3 in MeOH at room temperature to give 2 in 96% yield.
14. 12
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20. 2 at room temperature for 30 h produced 1 in 36% yield. The structures of other products are under investigation.
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