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Volumn 46, Issue 8, 2005, Pages 1281-1285

Efficient synthesis of enantiomerically pure dihydropyrans

Author keywords

Aldol; Dihydropyran; Enzyme; Metathesis; Synthesis

Indexed keywords

PYRAN DERIVATIVE;

EID: 19944430781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.128     Document Type: Article
Times cited : (12)

References (93)
  • 1
    • 13244294241 scopus 로고    scopus 로고
    • note
    • Crystallographic analysis of compound 12
  • 6
    • 0001867663 scopus 로고
    • For the preparation of (1) from ethyl-4,6-di-O-acetyl-2,3-dideoxy- α-erythro-hex-2-enopyranoside, see: (i) G. Grynkiewicz Carbohydr. Res. 128 1984 C9
    • (1984) Carbohydr. Res. , vol.128
    • Grynkiewicz, G.1
  • 67
    • 0001777309 scopus 로고    scopus 로고
    • Racemic mixtures of dihydropyrans were incubated with a lipase and vinyl acetate in toluene at room temperature. For a lipase resolution of tetrahydropyran derivatives, see: T. Oishi, Y. Nagumo, and M. Hirama Synlett 1997 980
    • (1997) Synlett , pp. 980
    • Oishi, T.1    Nagumo, Y.2    Hirama, M.3
  • 68
    • 0003610122 scopus 로고    scopus 로고
    • Wiley-VCH Weinheim
    • Lipase resolution of the hydroxy-dihydropyrans has not been reported. For reviews of the application of lipases and esterases in organic synthesis, see: U.T. Bornscheuer, and R.J. Kazlauskas Hydrolases in Organic Synthesis 1999 Wiley-VCH Weinheim
    • (1999) Hydrolases in Organic Synthesis
    • Bornscheuer, U.T.1    Kazlauskas, R.J.2
  • 71
    • 0035803694 scopus 로고    scopus 로고
    • Diols 10 and 11 and their racemates are important intermediates in the synthesis of many natural products and/or biologically active agents. For examples, see: Refs. 2 and 3 and K.C. Nicolaou, A. Vega Juan, and G. Vassilikogiannakis Angew. Chem., Int. Ed. 40 2001 4441
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4441
    • Nicolaou, K.C.1    Vega Juan, A.2    Vassilikogiannakis, G.3
  • 91
    • 0029957616 scopus 로고    scopus 로고
    • (a) Hydroxyester 12-17 were applied in the synthesis of biologically active deoxysugars, unpublished results, see: Ref. 25. (b) For the application of these derivatives to the synthesis of maitotoxin fragment, see: K.C. Nicolaou, M.H.D. Postema, E.W. Yue, and A. Nadin J. Am. Chem. Soc. 118 1996 10335
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10335
    • Nicolaou, K.C.1    Postema, M.H.D.2    Yue, E.W.3    Nadin, A.4
  • 92
    • 13244263829 scopus 로고    scopus 로고
    • note
    • f = 0.39 in 40% EtOAc-hexane) to give (-)-8 as a colorless liquid (6.87 g, 46%; >99.5% ee) and (-)-6 as a colorless liquid (5.64 g, 47%; 99.4% ee)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.