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Volumn , Issue 17, 2007, Pages 2651-2654

Nucleophilic additions and redox reactions of polyhydroxypyrroline N-oxides on the way to pyrrolidine alkaloids: Total synthesis of radicamine B

Author keywords

Alkaloids; Nitrones; Nucleophilic additions; Oxidations; Pyrrolidines

Indexed keywords

3,4 BIS(BENZYLOXY) 2 (BENZYLOXYMETHYL) 3,4 DIHYDRO 2H PYRROLE 1 OXIDE; PYRROLIDINE DERIVATIVE; RADICAMINE B; UNCLASSIFIED DRUG;

EID: 35648967109     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991059     Document Type: Article
Times cited : (40)

References (34)
  • 8
    • 84889478479 scopus 로고    scopus 로고
    • Iminosugars: From Synthesis to Therapeutic Applications; Wiley: Chichester
    • in press
    • (b) Compain, P.; Martin, O. R. Iminosugars: From Synthesis to Therapeutic Applications; Wiley: Chichester, 2007, in press.
    • (2007)
    • Compain, P.1    Martin, O.R.2
  • 15
    • 35648970633 scopus 로고    scopus 로고
    • See also ref. 5 and 6
    • (g) See also ref. 5 and 6.
  • 19
    • 35648997522 scopus 로고    scopus 로고
    • In their original papers, appeared during the preparation of this manuscript, Gurjar (ref. 5) and Yu (ref. 6) reported the synthesis of the enantiomers of the natural products since they started from ent-5, synthesizing ent-1 and ent-2. Indeed, Yu et al. (ref. 6) revised the configuration of both natural radicamines A and B as those given in Figure 1.
    • In their original papers, appeared during the preparation of this manuscript, Gurjar (ref. 5) and Yu (ref. 6) reported the synthesis of the enantiomers of the natural products since they started from ent-5, synthesizing ent-1 and ent-2. Indeed, Yu et al. (ref. 6) revised the configuration of both natural radicamines A and B as those given in Figure 1.
  • 25
    • 35649024303 scopus 로고    scopus 로고
    • Data for 8: [α]D20 +57 (c 1.11, H2O, 1H NMR (400 MHz, D2O, δ, 3.63 (ddd, J, 8.2, 5.5, 4.1 Hz, 1 H, H5, 3.83 (dd, J, 13.3, 6.3 Hz, 1 H, CH2OH, 3.88 (dd, J, 13.3, 4.5 Hz, 1 H, CH2OH, 4.11 (t, J, 7.5 Hz, 1 H, H4, 4.39 (d, J, 9.9 Hz, 1 H, H2, 4.43 (dd, J, 10.0, 6.9 Hz, 1 H, H3, 7.37-7.47 (m, 5 H, Ar, 13C NMR (100 MHz, D2O, δ, 58.1 (CH2OH, 61.9 (C2, 63.2 (C5, 73.7 (C3, 77.5 (C4, 128.3 (Ar, 128.5 (Ar, 130.3 (Ar, 131.3 Ar, Anal. Calcd for C11H 16NO3Cl: C, 53.77; H, 6.56; N, 5.70. Found: C, 53.92; H, 6.74; N, 5.68
    • 3Cl: C, 53.77; H, 6.56; N, 5.70. Found: C, 53.92; H, 6.74; N, 5.68.
  • 29
    • 35648990589 scopus 로고    scopus 로고
    • f = -79.21 kcal/mol).
    • f = -79.21 kcal/mol).
  • 31
    • 35648946901 scopus 로고    scopus 로고
    • Data for 15: [α]D20 +45 (c 0.41, H2O, 1H NMR (400 MHz, D2O, δ, 3.86-3.96 (m, 3 H, H5, CH2OH, 4.35 (t, J, 3.3 Hz, 1 H, H4, 4.41 (d, J, 5.9 Hz, 1 H, H2, 4.49 (dd, J, 5.9, 3.1 Hz, 1 H, H3, 7.40-7.50 (m, 5 H, Ar, 13C NMR (100 MHz, D2O, δ, 56.9 (CH2OH, 62.9 (C2, 67.6 (C5, 74.5 (C3, 79.8 (C 4, 128.4 (Ar, 129.4 (Ar, 130.0 (Ar, 132.1 (Ar, Anal. Calcd for C11H16NO3Cl: C, 53.77; H, 6.56; N, 5.70. Found: C, 53.70; H, 6.62; N, 5.79. Data for 16: [α]D 20 +78 (c 0.54, H2O, 1H NMR (400 MHz, D2O, δ, 3.64 (ddd, J, 8.4, 4.8, 3.5 Hz, 1 H, H 5, 3.85 dd, J, 12.2, 8.6 Hz, 1 H, CH2OH
    • 3Cl: C, 53.77; H, 6.56; N, 5.70. Found: C, 53.85; H, 6.40; N, 5.45.
  • 34
    • 35648969641 scopus 로고    scopus 로고
    • Data for 2·HCl: [α]D20 +81 (c 0.25, H2O, 1H NMR (400 MHz, D2O, δ, 3.57 (ddd, J, 4.0, 6.2, 8.5 Hz, 1 H, H5, 3.81 (dd, J, 6.2, 12.6 Hz, 1 H, CH2OH, 3.86 (dd, J, 4.0, 12.6 Hz, 1 H, CH2OH, 4.08 (t, J, 7.7 Hz, 1 H, H4, 4.31 (d, J, 10.2 Hz, 1 H, H2, 4.37 (dd, J, 7.5, 10.2 Hz, 1 H, H3, 6.87 (d, J, 8.7 Hz, 2 H, ArH, 7.32 (d, J, 8.7 Hz, 2 H, ArH, 13C NMR (100 MHz, D 2O, d, 58.2 (CH2OH, 61.6 (C2, 62.8 (C 4, 73.6 (C3, 77.1 (C5, 116.2 (Ar, 122.9 (Ar, 130.2 (Ar, 157.1 (Ar, Anal. Calcd for C11H 16NO4Cl: C, 50.48; H, 6.48; N, 5.63. Found: C, 58.29; H, 6.73; N, 5.80. Data for 2: [α]D20 +74 c 0.29, H
    • 4: C, 58.66; H, 6.71; N, 6.22. Found: C, 58.50; H, 6.90; N, 6.31.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.