Oxidative cyclization of 3-hydroxy-5-tri(butyl)stannylpentanoic acids to the corresponding δ-lactones

Synthesis

Volumn , Issue 8, 1997, Pages 937-941

  Yamamoto, Makoto ^a   Hirota, Masahiro ^a   Kishikawa, Keiki ^a   Kohmoto, Shigeo ^a   Yamada, Kazutoshi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030855954     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1286     Document Type: Article

References (16)

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3. 3 Oxidation: Itoh, A.; Saito, T.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn 1981, 54, 1456. PhI(O) Oxidation: Ochiai, M.; Ukita, T.; Nagao, Y.; Fujita, E. J. Chem. Soc., Chem. Commun. 1984, 1007.
4. 3 Oxidation: Itoh, A.; Saito, T.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn 1981, 54, 1456. PhI(O) Oxidation: Ochiai, M.; Ukita, T.; Nagao, Y.; Fujita, E. J. Chem. Soc., Chem. Commun. 1984, 1007.
5. 3 Oxidation: Itoh, A.; Saito, T.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn 1981, 54, 1456. PhI(O) Oxidation: Ochiai, M.; Ukita, T.; Nagao, Y.; Fujita, E. J. Chem. Soc., Chem. Commun. 1984, 1007.
6. 3 Oxidation: Itoh, A.; Saito, T.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn 1981, 54, 1456. PhI(O) Oxidation: Ochiai, M.; Ukita, T.; Nagao, Y.; Fujita, E. J. Chem. Soc., Chem. Commun. 1984, 1007.
7. 3 Oxidation: Itoh, A.; Saito, T.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn 1981, 54, 1456. PhI(O) Oxidation: Ochiai, M.; Ukita, T.; Nagao, Y.; Fujita, E. J. Chem. Soc., Chem. Commun. 1984, 1007.
8. 3 Oxidation: Itoh, A.; Saito, T.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn 1981, 54, 1456. PhI(O) Oxidation: Ochiai, M.; Ukita, T.; Nagao, Y.; Fujita, E. J. Chem. Soc., Chem. Commun. 1984, 1007.
9. 3 Oxidation: Itoh, A.; Saito, T.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn 1981, 54, 1456. PhI(O) Oxidation: Ochiai, M.; Ukita, T.; Nagao, Y.; Fujita, E. J. Chem. Soc., Chem. Commun. 1984, 1007.
10. 3 Oxidation: Itoh, A.; Saito, T.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn 1981, 54, 1456. PhI(O) Oxidation: Ochiai, M.; Ukita, T.; Nagao, Y.; Fujita, E. J. Chem. Soc., Chem. Commun. 1984, 1007.
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12. For example, the LTA treatment of 5-tri(butyl)stannylpentanol gave the corresponding 5-acetoxylated pentanol, and none of the cyclized tetrahydropyran was detected. (M. Yamamoto, unpublished results).
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