Four-step convergent synthesis of trans-fused tetracyclic oxane

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 507-508

  Fujiwara, Kenshu ^a   Morishita, Hiroshi ^a   Saka, Kimiko ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Coupling reactions; Etherification; Oxygen heterocycles; Polyethers

Indexed keywords

ACETAL; DIKETONE; ETHER DERIVATIVE;

ARTICLE; COUPLING FACTOR; CYCLIZATION; DRUG SYNTHESIS; ESTERIFICATION; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034700814     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02102-4     Document Type: Article

References (14)

1. For reviews for natural polycyclic ethers, see: (a) Shimizu, Y. Chem. Rev. 1993, 93, 1685. (b) Yasumono, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
2. For reviews for natural polycyclic ethers, see: (a) Shimizu, Y. Chem. Rev. 1993, 93, 1685. (b) Yasumono, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
3. For recent convergent approaches to polycyclic oxanes, see: (a) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (b) Alvarez, E.; Pérez, R.; Rico, M.; Rodríguez, R. M.; Martín, J. D. J. Org. Chem. 1996, 61, 3003. (c) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (d) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037.
4. For recent convergent approaches to polycyclic oxanes, see: (a) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (b) Alvarez, E.; Pérez, R.; Rico, M.; Rodríguez, R. M.; Martín, J. D. J. Org. Chem. 1996, 61, 3003. (c) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (d) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037.
5. For recent convergent approaches to polycyclic oxanes, see: (a) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (b) Alvarez, E.; Pérez, R.; Rico, M.; Rodríguez, R. M.; Martín, J. D. J. Org. Chem. 1996, 61, 3003. (c) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (d) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037.
6. For recent convergent approaches to polycyclic oxanes, see: (a) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. (b) Alvarez, E.; Pérez, R.; Rico, M.; Rodríguez, R. M.; Martín, J. D. J. Org. Chem. 1996, 61, 3003. (c) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027. (d) Fujiwara, K.; Saka, K.; Takaoka, D.; Murai, A. Synlett 1999, 1037.
7. Oxane 7 was prepared from the corresponding benzyl ethereal derivative reported by Hirama (Oishi, T.; Nagumo, Y.; Hirama, M. Synlett 1997, 980).
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13. For the reported synthesis and reductive etherification of trans-fused tetracyclic dithioacetals, see: Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; Defrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040.
14. H5-6e (5.0 Hz) which suggested the chair conformations of the central oxane rings.