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Volumn 39, Issue 2, 2000, Pages 355-357

Hydroxy-directed, SmI2-induced conversion of carbohydrates into carbocycles

Author keywords

Carbohydrates; Chelation control; Cyclizations; Samarium diiodide; Synthetic methods

Indexed keywords

ALKENE; CARBOHYDRATE DERIVATIVE; CYCLOHEXANE DERIVATIVE; GLUCOPYRANOSIDE; SAMARIUM DIIODIDE;

EID: 0034677075     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000117)39:2<355::AID-ANIE355>3.0.CO;2-U     Document Type: Article
Times cited : (31)

References (39)
  • 1
    • 0346131378 scopus 로고
    • Samarium(II) iodide has evolved as a unique, single-electron reducing reagent for inducing reductive couplings to effectively form carbon -carbon bonds under exceedingly mild conditions; reviews: a) H. B. Kagan, M. Sasaki, J. Collin, Pure Appl. Chem. 1988, 60, 1725;
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1725
    • Kagan, H.B.1    Sasaki, M.2    Collin, J.3
  • 16
    • 0041133877 scopus 로고    scopus 로고
    • 2-mediated 5- and 6-exo-trig cyclizations stereocontrolled by hydroxy groups were reported: G. A. Molander, C. P. Losada, J. Org. Chem. 1997, 62, 2934.
    • (1997) J. Org. Chem. , vol.62 , pp. 2934
    • Molander, G.A.1    Losada, C.P.2
  • 33
    • 0343026708 scopus 로고    scopus 로고
    • note
    • 2AlH, 3) chlorination, 4) substitution with NaSPh, and 5) desilylation. Following the same procedure, the α,β-unsaturated ester 15 and sulfide 4 were derived from methyl β-D-galactopyranoside.
  • 36
    • 0342592552 scopus 로고    scopus 로고
    • note
    • The stereostructures of cyclohexanediols 2, 3, 5, and 6 and cyclopentanols 14, 16, and 17 were confirmed by 2D COSY and 2D NOESY experiments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.