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Volumn 45, Issue 29, 2004, Pages 5673-5676

Synthesis of iodinated analogues of all trans retinoic acid (ATRA) for SPECT imaging

Author keywords

Cross coupling; Iodine; Labelling; Retinoic

Indexed keywords

IODINE; METHYL GROUP; RETINOIC ACID; RETINOIC ACID DERIVATIVE;

EID: 3042630883     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.103     Document Type: Article
Times cited : (6)

References (33)
  • 4
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    • Eur. Patent Appl. No 728742, 1996
    • For a derivative of 9-cis retinoic acid in which iodine substitutes a vinylic hydrogen see: Klaus, M.; Lovey, A. J.; Mohr, P.; Rosenberg, M. Eur. Patent Appl. No 728742, 1996
    • Klaus, M.1    Lovey, A.J.2    Mohr, P.3    Rosenberg, M.4
  • 5
    • 0037430575 scopus 로고    scopus 로고
    • This compound has recently been obtained by a free-radical approach; see:
    • This compound has recently been obtained by a free-radical approach; see: Commeiras L., Santelli M., Parrain J.-L. Tetrahedron Lett. 44:2003;2311
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2311
    • Commeiras, L.1    Santelli, M.2    Parrain, J.-L.3
  • 7
    • 0001034015 scopus 로고
    • Red-Al has been shown to be the reagent of choice for this transformation:
    • Red-Al has been shown to be the reagent of choice for this transformation: Denmark S.E., Jones T.K. J. Org. Chem. 47:1982;4595
    • (1982) J. Org. Chem. , vol.47 , pp. 4595
    • Denmark, S.E.1    Jones, T.K.2
  • 11
    • 0030199618 scopus 로고    scopus 로고
    • The Z configuration of
    • The Z configuration of 3 has been secured by its conversion to nakienone B. See: Pour M., Negishi E.-I. Tetrahedron Lett. 37:1996;4679
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4679
    • Pour, M.1    Negishi, E.-I.2
  • 13
    • 3042625197 scopus 로고    scopus 로고
    • note
    • 3), 72.3 (C-4), 128.8 (C-3), 129.1(C-2), 196.5 (C-1) can be purified by column chromatography but should be freshly prepared before use
  • 15
    • 3042574144 scopus 로고    scopus 로고
    • note
    • 3), 71.7 (C-8), 111.7 (C-7), 120.6 (C-2), 131.1, 135.1, 138.8 (C-4, C-5, C-6), 151.7 (C-3), 166.8 (C-1)
  • 16
    • 3042527751 scopus 로고    scopus 로고
    • note
    • In contrast to oxidation of 3, the use of IBX resulted here in configurational scrambling as a 1:1.8 E/Z mixture was detected
  • 23
    • 0021025690 scopus 로고
    • 3-1), 33.2 (C-4), 34.3 (C-1), 39.7 (C-2), 124.7 (C-13), 127.0, 128.6, 128.7, 130.5, 145.2 (C-7, C-10, C-11, C-12, C-14), 130.9 (C-5), 137.0 (C-8), 137.6 (C-6), 143.6 (C-9), 168.0 (C-15)
    • (1983) J. Org. Chem. , vol.48 , pp. 3164
    • Bernard, M.1    Ford, W.T.2    Nelson, E.C.3
  • 24
    • 3042669497 scopus 로고    scopus 로고
    • note
    • 3-1), 33.2 (C-4), 34.3 (C-1), 39.7 (C-2), 124.7 (C-13), 127.0, 128.6, 128.7, 130.5, 145.2 (C-7, C-10, C-11, C-12, C-14), 130.9 (C-5), 137.0 (C-8), 137.6 (C-6), 143.6 (C-9), 168.0 (C-15)
  • 27
    • 0000991678 scopus 로고
    • O-TMS propargyl alcohol is very moisture sensitive and was directly used after in situ formation that is without isolation. For use of a tert-butyldimethylsilyl ether, see:
    • O-TMS propargyl alcohol is very moisture sensitive and was directly used after in situ formation that is without isolation. For use of a tert-butyldimethylsilyl ether, see: Piers E., Chong M., Morton H.E. Tetrahedron. 45:1989;363
    • (1989) Tetrahedron , vol.45 , pp. 363
    • Piers, E.1    Chong, M.2    Morton, H.E.3
  • 30
    • 3042669498 scopus 로고    scopus 로고
    • note
    • Under those conditions, NMR analysis of the crude material showed 92% E configurational purity; note that a 6 to 4:1 E/Z ratio was observed after reaction with the ylide derived from 9 (see Ref. 19)
  • 32
    • 3042530121 scopus 로고    scopus 로고
    • note
    • The less toxic bis(tributyl)ditin was ineffective for this transformation
  • 33
    • 3042571787 scopus 로고    scopus 로고
    • note
    • 2/Pd (0), 73%); 2 could be regenerated (90%) after reaction with iodine


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.