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Volumn 45, Issue 5, 2004, Pages 955-957

Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone

Author keywords

Amino alcohols; Asymmetric synthesis; Cytoxazone; Immunosuppressive compounds; Natural products

Indexed keywords

AMINOALCOHOL; CINNAMIC ACID DERIVATIVE; CYTOXAZONE; EPICYTOXAZONE; METHYL 4 METHOXYCINNAMATE; NATURAL PRODUCT; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0346392218     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.096     Document Type: Article
Times cited : (45)

References (26)
  • 12
    • 0034697199 scopus 로고    scopus 로고
    • For a review article on the synthesis of vicinal aminoalcohols, see:
    • For a review article on the synthesis of vicinal aminoalcohols, see: Bergmeier S.C. Tetrahedron. 56:2000;2561-2576.
    • (2000) Tetrahedron , vol.56 , pp. 2561-2576
    • Bergmeier, S.C.1
  • 15
    • 0037124555 scopus 로고    scopus 로고
    • For a critical overview and comparison of various methodologies for enantioselective oxidations of alkenes, see:
    • For a critical overview and comparison of various methodologies for enantioselective oxidations of alkenes, see: Bonini C., Righi G. Tetrahedron. 58:2002;4981-5021.
    • (2002) Tetrahedron , vol.58 , pp. 4981-5021
    • Bonini, C.1    Righi, G.2
  • 17
    • 0034676672 scopus 로고    scopus 로고
    • It is known that N-Boc-amides can be transformed directly into oxazolidinones with configurational inversion at the hydroxyl bearing carbon atom: however, due to the bulky nature of the t-Boc protecting group, the AA reaction with N-Boc-N-halocarbamates is not successful, and the preparation of the N-Boc analogue of
    • It is known that N-Boc-amides can be transformed directly into oxazolidinones with configurational inversion at the hydroxyl bearing carbon atom: Benedetti F., Norbedo S. Tetrahedron Lett. 41:2000;10071-10074. however, due to the bulky nature of the t-Boc protecting group, the AA reaction with N-Boc-N-halocarbamates is not successful, and the preparation of the N-Boc analogue of 4 would require additional steps.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 10071-10074
    • Benedetti, F.1    Norbedo, S.2
  • 19
    • 85030930652 scopus 로고    scopus 로고
    • In addition to the amidoalcohol 4 , methyl (2S,3R)-2,3-dihydroxy-3-(4- methoxyphenyl)-propanoate, the AD product, was isolated in 13% yield.
  • 26
    • 85030929707 scopus 로고    scopus 로고
    • The optical purity of the product, determined by chiral HPLC as described in Ref. 9, was found to be >98%
    • The optical purity of the product, determined by chiral HPLC as described in Ref. 9, was found to be >98%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.