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Volumn 66, Issue 27-28, 2010, Pages 4965-4969

Enantioselective total synthesis of idesolide via NaHCO3- promoted dimerization

Author keywords

Antiinflammatory; Dimerization; Idesolide; Spiro compounds; Total synthesis

Indexed keywords

1 (HYDROXYMETHYL) 7 OXABICYCLO[4.1.0]HEPTAN 2 ONE; ALCOHOL; BICARBONATE; DIMETHYL 3A,6,7,7A TETRAHYDRO 2',7A DIHYDROXYSPIRO[1,3 BENZODIOXOLE 2,1' [3]CYCLOHEXENE] 2'3A DICARBOXYLATE; IDESOLIDE; METHYL 1 HYDROXY 6 OXO 2 CYCLOHEXENE 1 CARBOXYLATE; METHYL 1,2 DIHYDROXYCYCLOHEXANE 1 CARBOXYLATE; METHYL 2 (TERT BUTYLDIMETHYLSILYLOXY) 7 OXABICYCLO[4.1.0]HEPTANE 1 CARBOXYLATE; METHYL 2 HYDROXY 7 OXABICYCLO[4.1.0]HEPTANE 1 CARBOXYLATE; METHYL 2 OXO 7 OXABICYCLO[4.1.0 OXABICYCLO[4.1.0]HEPTANE 1 CARBOXYLATE; METHYL 6 (TERT BUTYLDIMETHYLSILYLOXY) 1 HYDROXY 2 CYCLOHEXENE 1 CARBOXYLIC ACID; MONOMER; UNCLASSIFIED DRUG;

EID: 77954349011     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.034     Document Type: Article
Times cited : (21)

References (38)
  • 5
    • 77954349364 scopus 로고    scopus 로고
    • For examples, see:
    • For examples, see:
  • 26
    • 77954349216 scopus 로고    scopus 로고
    • 2O gave a complex mixture in the former conditions and a 12% yield of 8c in the latter.For reaction conditions, see:
    • 2O gave a complex mixture in the former conditions and a 12% yield of 8c in the latter.For reaction conditions, see:
  • 30
    • 77954349515 scopus 로고    scopus 로고
    • 2O, and DIBAL/THF at -78 °C afforded epimeric mixtures of 11β and 11α in ratios of 1:1.2 (83% yield), 1:1.7 (94% yield), and 1:1.8 (63% yield), respectively, favoring 11α
    • 2O, and DIBAL/THF at -78 °C afforded epimeric mixtures of 11β and 11α in ratios of 1:1.2 (83% yield), 1:1.7 (94% yield), and 1:1.8 (63% yield), respectively, favoring 11α.
  • 33
    • 77954348502 scopus 로고    scopus 로고
    • The established absolute stereochemistry of 15α means that the Sharpless asymmetric epoxidation of the electron deficient olefin 5 proceeded in accordance with the general enantioface selection rule. For only a few precedents of the asymmetric epoxidation of electron deficient alkenes, see:
    • The established absolute stereochemistry of 15α means that the Sharpless asymmetric epoxidation of the electron deficient olefin 5 proceeded in accordance with the general enantioface selection rule. For only a few precedents of the asymmetric epoxidation of electron deficient alkenes, see:
  • 36
    • 77954348775 scopus 로고    scopus 로고
    • Several hours after the start of the reaction, the spinning of the magnetic stirring bar stopped, because the viscosity of the reaction mixture increased as the dimerization proceeded. Therefore, the mixture was, actually, left to stand for the rest of the reaction time
    • Several hours after the start of the reaction, the spinning of the magnetic stirring bar stopped, because the viscosity of the reaction mixture increased as the dimerization proceeded. Therefore, the mixture was, actually, left to stand for the rest of the reaction time.
  • 37
    • 77954348944 scopus 로고    scopus 로고
    • 13C NMR spectra previously reported by Iwabuchi and co-workers; see Ref. 7
    • 13C NMR spectra previously reported by Iwabuchi and co-workers; see Ref. 7.
  • 38
    • 77954349276 scopus 로고    scopus 로고
    • 3 from 2 equiv to 4 equiv did not improve the chemical yield further
    • 3 from 2 equiv to 4 equiv did not improve the chemical yield further.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.