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Volumn 39, Issue 7, 2000, Pages 1234-1236

Ring-closing alkyne metathesis: Application to the stereoselective total synthesis of prostaglandin E2-1,15-lactone

Author keywords

Alkynes; Macrocycles; Metathesis; Prostaglandins; Total synthesis

Indexed keywords

ALKENE; ALKYNE; CYCLOALKENE; LACTONE DERIVATIVE; MACROCYCLIC COMPOUND; PROSTAGLANDIN E2 DERIVATIVE;

EID: 0038584256     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000403)39:7<1234::AID-ANIE1234>3.0.CO;2-V     Document Type: Article
Times cited : (87)

References (54)
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    • 13C NMR data. Careful analysis of the crude product by HPLC, however, shows that the purity is only about 90%. This material can be used directly in the next step, because the isomeric by-products do not undergo productive 1,4-addition, see: C. R. Johnson, T. D. Penning. J. Am. Chem. Soc. 1988, 110, 4726-4735.
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    • 2, and imidazole according to a literature procedure: G. L. Lange, C. Gottardo, Synth. Commun. 1990, 20, 1473-1479;
    • (1990) Synth. Commun. , vol.20 , pp. 1473-1479
    • Lange, G.L.1    Gottardo, C.2
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    • Determined by HPLC on a Chiracel OD-H column with n-heptane/2-propanol as mobile phase
    • a) Determined by HPLC on a Chiracel OD-H column with n-heptane/2-propanol as mobile phase.
  • 46
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    • Determined by HPLC on a Chiralpak AD column with n-heptane/2-propanol (95:5) as mobile phase
    • b) Determined by HPLC on a Chiralpak AD column with n-heptane/2-propanol (95:5) as mobile phase.
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    • note
    • +], 1), 431 (1), 389 (33), 317 (18), 297 (8), 225 (5), 155 (5), 129 (10), 91(12), 75 (100)
  • 48
    • 85003509098 scopus 로고    scopus 로고
    • 4Si (446.71): C 69.91, H 9.48; found: C 70.08, H 9.42
    • 4Si (446.71): C 69.91, H 9.48; found: C 70.08, H 9.42.
  • 50
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    • We consider the "economy of steps" as a strategic goal for target oriented syntheses in general, see: A. Fürstner, Synlett 1999, 1523-1533.
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    • Fürstner, A.1
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    • note
    • +], 24), 316 (38), 298 (13), 262 (39), 208 (63), 163 (64), 151 (22), 145 (15),133 (25), 121 (28), 107 (42), 91 (78), 79 (100), 67 (83), 55 (93).
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    • For a study on the solid phase synthesis of prostaglandin derivatives and of small prostaglandin libraries see: a) L. A. Thompson, F. L. Moore, Y. C. Moon, J. A. Ellman, J. Org. Chem. 1998, 63, 2066-2067;
    • (1998) J. Org. Chem. , vol.63 , pp. 2066-2067
    • Thompson, L.A.1    Moore, F.L.2    Moon, Y.C.3    Ellman, J.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.