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Volumn 38, Issue 43, 1997, Pages 7511-7514

An efficient catalytic stereoselective route to a key intermediate for the synthesis of the long-lived PGI2 analog ZK 96480 (Cicaprost(TM))

Author keywords

[No Author keywords available]

Indexed keywords

CICAPROST; PROSTACYCLIN DERIVATIVE;

EID: 0030841352     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01803-0     Document Type: Article
Times cited : (33)

References (27)
  • 4
    • 0343531071 scopus 로고    scopus 로고
    • Personal communication to E.J.C. from the PPH Cure Foundation, Washington, DC, a non-profit organization
    • Personal communication to E.J.C. from the PPH Cure Foundation, Washington, DC, a non-profit organization.
  • 8
    • 0001513454 scopus 로고    scopus 로고
    • For other oxazaborolidine-catalyzed reductions of alkynyl ketones see: (a)
    • For other oxazaborolidine-catalyzed reductions of alkynyl ketones see: (a) Parker, K.A.; Ledeboer, M.W. J. Org. Chem. 1996, 61, 3214.
    • (1996) J. Org. Chem. , vol.61 , pp. 3214
    • Parker, K.A.1    Ledeboer, M.W.2
  • 11
  • 13
    • 0030570857 scopus 로고    scopus 로고
    • For other examples of oxazaborolidine-catecholborane reductions that give improved enantioselectivity at higher temperatures see: (a)
    • For other examples of oxazaborolidine-catecholborane reductions that give improved enantioselectivity at higher temperatures see: (a) Corey, E.J.; Helal, C.J. Tetrahedron Lett. 1996, 37, 5675.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5675
    • Corey, E.J.1    Helal, C.J.2
  • 14
    • 0343966933 scopus 로고    scopus 로고
    • (b) reference 8
    • (b) reference 8.
  • 15
    • 0343531056 scopus 로고    scopus 로고
    • Available from the Aldrich Chemical Company
    • Available from the Aldrich Chemical Company.
  • 17
    • 0343991943 scopus 로고    scopus 로고
    • The volatility of iodide 11 and alkynyl ester 12 required solvent removal at 0 °C/50 mmHg
    • The volatility of iodide 11 and alkynyl ester 12 required solvent removal at 0 °C/50 mmHg.
  • 19
    • 0000904191 scopus 로고
    • (a) For a different preparation of this zinc homoenolate see
    • (a) For a different preparation of this zinc homoenolate see: Nakamura, E.; Sekiya, K.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 337.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 337
    • Nakamura, E.1    Sekiya, K.2    Kuwajima, I.3
  • 20
    • 4243489506 scopus 로고
    • (b) For an excellent review on the preparation and reactions of organozinc reagents, see
    • (b) For an excellent review on the preparation and reactions of organozinc reagents, see: Knochel, P.; Singer, R.D. Chem. Rev. 1993, 93, 2117.
    • (1993) Chem. Rev. , vol.93 , pp. 2117
    • Knochel, P.1    Singer, R.D.2
  • 22
    • 0000064055 scopus 로고
    • This coupling is based upon that reported by
    • This coupling is based upon that reported by: Yeh, M.C.P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4799
    • Yeh, M.C.P.1    Knochel, P.2
  • 24
    • 33845556993 scopus 로고
    • Triisopropylsilylacetylene was prepared via the reaction between lithium acetylide and triisopropylsilyl chloride. See
    • Triisopropylsilylacetylene was prepared via the reaction between lithium acetylide and triisopropylsilyl chloride. See: Bottaro, J.C.; Hanson, R.N.; Seitz, D.E. J. Org. Chem. 1981, 46, 5221.
    • (1981) J. Org. Chem. , vol.46 , pp. 5221
    • Bottaro, J.C.1    Hanson, R.N.2    Seitz, D.E.3
  • 25
    • 0342685613 scopus 로고    scopus 로고
    • Note
    • t: 29.8 min, major; 35.6 min, minor).
  • 26
    • 0342685611 scopus 로고    scopus 로고
    • The relative stereochemistry of the reduction of ketone 14 to alcohol 2 was assigned by analogy with the reduction of ketone 6 to alcohol 8
    • The relative stereochemistry of the reduction of ketone 14 to alcohol 2 was assigned by analogy with the reduction of ketone 6 to alcohol 8.
  • 27
    • 0343119887 scopus 로고    scopus 로고
    • This research was supported by grants from the National Institutes of Health and the National Science Foundation
    • This research was supported by grants from the National Institutes of Health and the National Science Foundation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.