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Volumn 67, Issue 27-28, 2011, Pages 5083-5097

Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: Applications for the synthesis of leucascandrolide A macrolactone

Author keywords

Asymmetric induction; Boron auxiliary; Nonracemic 1,5 diols; S E reactions; Tetrahydropyran synthesis

Indexed keywords

LACTONE DERIVATIVE; LEUCASCANDROLIDE A; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79958707669     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.020     Document Type: Article
Times cited : (19)

References (58)
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    • The preparation of epoxide 19 utilized (R)-epichlorohydrin (97% ee, Aldrich) by adapting the earlier reports of Seebach, co-workers
    • The preparation of epoxide 19 utilized (R)-epichlorohydrin (97% ee, Aldrich) by adapting the earlier reports of Seebach, co-workers. Seebach, D.; Willert, I.; Beck, A. K.; Gröbel, B.-T. Helv. Chim. Acta 1978, 61, 2510.
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  • 37
    • 79958728682 scopus 로고    scopus 로고
    • (4R,5R)-2-Bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3, 2-diazaborolidine
    • For information regarding the preparation of 21: Posted October 15
    • For information regarding the preparation of 21: Williams, D. R.; Kammler, D. C.; (4R,5R)-2-Bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl- 1,3,2-diazaborolidine. e-EROS Encyclopedia of Reagents for Organic Synthesis [Online]; John Wiley & Sons, Ltd., Posted October 15, 2002. http://onlinelibrary.wiley.com/o/eros/articles/rn00115/frame.html.
    • (2002) e-EROS Encyclopedia of Reagents for Organic Synthesis [Online]
    • Williams, D.R.1    Kammler, D.C.2
  • 40
    • 0000569383 scopus 로고
    • The chiral oxirane building block 34 was conveniently produced via the known reduction of d-malic acid (i). See
    • The chiral oxirane building block 34 was conveniently produced via the known reduction of d-malic acid (i). See: Hanessian, S.; Ugolini, A.; Dube, D.; Glamyan, A. Can. J. Chem. 1984, 62, 2146;
    • (1984) Can. J. Chem. , vol.62 , pp. 2146
    • Hanessian, S.1    Ugolini, A.2    Dube, D.3    Glamyan, A.4
  • 41
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    • Selective conversion of (R)-1,2,4-butanetriol to the primary tert-butyldimethylsilyl ether ii utilized the published dibutylstannanediyl acetal method. See: Monotosylation and treatment with NaH provided 34 in excellent overall yield. (Chemical Equation Presented)
    • Selective conversion of (R)-1,2,4-butanetriol to the primary tert-butyldimethylsilyl ether ii utilized the published dibutylstannanediyl acetal method. See: Leigh, D.; Martin, R. P.; Smart, J. P.; Truscello, A. M. J. Chem. Soc., Chem. Commun. 1994, 1373 Monotosylation and treatment with NaH provided 34 in excellent overall yield. (Chemical Equation Presented)
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 1373
    • Leigh, D.1    Martin, R.P.2    Smart, J.P.3    Truscello, A.M.4
  • 46
    • 2342530383 scopus 로고    scopus 로고
    • The model studies of Table 1 have previously been published as part of an extensive investigation of this SE′ methodology
    • The model studies of Table 1 have previously been published as part of an extensive investigation of this SE′ methodology: Williams, D. R.; Meyer, K. G.; Shamim, K.; Patnaik, S. Can. J. Chem. 2004, 82, 120.
    • (2004) Can. J. Chem. , vol.82 , pp. 120
    • Williams, D.R.1    Meyer, K.G.2    Shamim, K.3    Patnaik, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.