Synthetic research on cyclitols using C6-chiron, 6-(benzyloxy)-3- cyclohexen-1-ol: A concise and highly diastereoselective synthesis of (-)- gala-quercitol

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3781-3784

  Maezaki, Naoyoshi ^a   Nagahashi, Noboru ^a   Yoshigami, Ryoko ^a   Iwata, Chuzo ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C6 Chiron; Cyclitols; Epoxide; Gala Quercitol; Isomerization

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; QUERCETIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENZYME INHIBITION; GENE REARRANGEMENT; HYDROXYLATION; OXYGENATION; PROMOTER REGION; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0033531992     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00608-5     Document Type: Article

References (22)

1. 6-chirons for the synthesis of cyclitols, see: O'Brien, P.; Poumellec, P. J. Chem. Soc, Perkin Trans. 1, 1998, 2435-2441; T. Hudticky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000 ; Takano, S.; Moriya, M.; Higashi, Y.;Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 177-178; Drian, C. L.; Vionnet, J.-P.; Vogel, P. Helv. Chim. Acta 1990, 73, 161-163.
2. 6-chirons for the synthesis of cyclitols, see: O'Brien, P.; Poumellec, P. J. Chem. Soc, Perkin Trans. 1, 1998, 2435-2441; T. Hudticky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000 ; Takano, S.; Moriya, M.; Higashi, Y.;Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 177-178; Drian, C. L.; Vionnet, J.-P.; Vogel, P. Helv. Chim. Acta 1990, 73, 161-163.
3. 6-chirons for the synthesis of cyclitols, see: O'Brien, P.; Poumellec, P. J. Chem. Soc, Perkin Trans. 1, 1998, 2435-2441; T. Hudticky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000 ; Takano, S.; Moriya, M.; Higashi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 177-178; Drian, C. L.; Vionnet, J.-P.; Vogel, P. Helv. Chim. Acta 1990, 73, 161-163.
4. 6-chirons for the synthesis of cyclitols, see: O'Brien, P.; Poumellec, P. J. Chem. Soc, Perkin Trans. 1, 1998, 2435-2441; T. Hudticky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000 ; Takano, S.; Moriya, M.; Higashi, Y.;Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 177-178; Drian, C. L.; Vionnet, J.-P.; Vogel, P. Helv. Chim. Acta 1990, 73, 161-163.
5. 2. Maezaki, N.; Sakamoto, A.; Soejima, M.; Sakamoto, I.; Li, Y. X.; Tanaka. T.; Ohishi, H.; Sakaguchi, K.; Iwata, C. Tetrahedron: Asymmetry 1996, 7, 2787-2790 and references cited therein . The enantiomer of 1 was synthesized by Fujioka and co-workers, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H.; Kita, Y. Tetrahedron Lett. 1998, 39, 7309-7312.
6. 2. Maezaki, N.; Sakamoto, A.; Soejima, M.; Sakamoto, I.; Li, Y. X.; Tanaka. T.; Ohishi, H.; Sakaguchi, K.; Iwata, C. Tetrahedron:Asymmetry 1996, 7, 2787-2790 and references cited therein . The enantiomer of 1 was synthesized by Fujioka and co-workers, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H.; Kita, Y. Tetrahedron Lett. 1998, 39, 7309-7312.
7. 3. Recently, a highly anti-selective epoxidation of fully protected cis-4-cyclohexene-1,2-diols with dioxirane was reported: see, Sousa, S. E.; Kee, A.; O'Brien, P.; Watson, S. T. Tetrahedron Lett. 1999, 40, 387-390; Sousa, S. E.; O'Brien, P.; Pilgram, C. D.; Roder, D.; Towers, T. D. ibid. 1999, 40, 391-392.
8. 3. Recently, a highly anti-selective epoxidation of fully protected cis-4-cyclohexene-1,2-diols with dioxirane was reported: see, Sousa, S. E.; Kee, A.; O'Brien, P.; Watson, S. T. Tetrahedron Lett. 1999, 40, 387-390; Sousa, S. E.; O'Brien, P.; Pilgram, C. D.; Roder, D.; Towers, T. D. ibid. 1999, 40, 391-392.
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22. 5+H 165.0762. Found 165.0754.