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Volumn 46, Issue 17, 1990, Pages 6167-6184

Regio- and stereoselective conjugate addition of nitrogen nucleophiles to 2-alkenyl n-methylthiazolium iodides. synthesis of d-3-epi-daunosamine and some lincosamine analogues

Author keywords

[No Author keywords available]

Indexed keywords

DAUNOSAMINE DERIVATIVE; LINCOSAMINE DERIVATIVE;

EID: 0024998611     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)87939-4     Document Type: Article
Times cited : (18)

References (66)
  • 1
    • 77956948298 scopus 로고
    • Organic Synthesis with Sulfur Heterocycles (Thiazoles) as Auxiliaries. The Thiazole Route to Carbohydrates and Biologically Active Derivatives
    • Thiazole Route to Carbohydrates : Synthesis of building blocks or precursors to carbohydrates and related compounds using functionally substituted thiazoles. For recent accounts see :
    • (1989) Phosphorus, Sulfur, and Silicon and the Related Elements , vol.43 , pp. 25
    • Dondoni1
  • 11
    • 84918147768 scopus 로고    scopus 로고
    • The mercury-mediated hydrolysis of the thiazolidine ring to the formyl group does not tolerate a free amino group. The conversion to an amidic function such as N-Boc (ref. 2a) or N-Acetyl Dondoni, A. Fantin, G. Fogagnolo, M. Medici, A. Pedrini, P. Tetrahedron,1988, 44 3215, overcomes this problem
  • 12
    • 84918147767 scopus 로고    scopus 로고
    • The low isolated yield of 8c asks for modified conditions to make this functionalization synthetically useful.
  • 18
    • 84918147766 scopus 로고    scopus 로고
    • Results from our ongoing work in this area will be published in due course.
  • 38
    • 84918147765 scopus 로고    scopus 로고
    • The degree of selectivity was not improved by addition of LiBr and the change of the solvent ( methylene dichloride, 1,2-dichloroethane, chloroform, THF, DMF) and base ( n-BuLi, THF). Z- selectivity (90 : 10) was observed using the preformed phosphorane 1 in methanol as described.
  • 44
    • 84918147764 scopus 로고    scopus 로고
    • No reaction was observed between benzylamine and the 2-alkenylthiazole 10a in methanol after 48 hours at room temperature.
  • 45
    • 84918147763 scopus 로고    scopus 로고
    • Because of the various manipulations of the reaction mixture, it is very likely that the actual diastereoselectivity is higher than the quoted value.
  • 46
    • 84918180280 scopus 로고
    • It is worth pointing out that the stereochemical aspects of the nucleophilic conjugate addition to chiral α, β-unsaturated compounds activated by an electron-withdrawing group, is a rather complex and intriguing matter. Syn- and anti-selectivity may depend upon several factors including : i, the olefin geometry; ii) the nature and position of the asymmetric centre(s); iii) the nature of the activating group; iv) the type of nucleophile. See for instance ref. 15e and 16. See also
    • (1989) J.C.S. Chem. Commun. , pp. 91
    • Larcheveque1    Tamagnau2    Petit3
  • 48
    • 37049112080 scopus 로고
    • Asymmetric synthesis. Part 6. Copper salt promoted grignard reagent additions to ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate and subsequent formation of optically active 2-alkyl (or aryl) butane-1,4-dioic acids and butyro-1,4-lactones
    • (1983) Journal of the Chemical Society, Perkin Transactions 1 , pp. 2629
    • Lawston1    Inch2
  • 50
    • 49949128203 scopus 로고
    • Torsional strain involving partial bonds. The stereochemistry of the lithium aluminium hydride reduction of some simple open-chain ketones
    • (1968) Tetrahedron Letters , pp. 2199
    • Cherest1    Felkin2    Prudent3
  • 56
    • 0001232768 scopus 로고
    • For an excellent review on the synthesis of these amino sugars, see ref. 10b. For recent papers see ref. 11f and :
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1269
    • Danishefsky1    Maring2
  • 65
    • 84918147761 scopus 로고    scopus 로고
    • For the synthesis of lincosamine see ref. 13d and references cited therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.