메뉴 건너뛰기




Volumn 64, Issue 8, 1999, Pages 2776-2788

Applications of 5-endo-trigonal cyclization: Construction of compounds relevant to the synthesis of prostaglandins and methyl epi-jasmonate

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE DERIVATIVE; JASMONIC ACID; METHYL EPI JASMONATE; PROSTAGLANDIN; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033574499     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982225m     Document Type: Article
Times cited : (35)

References (67)
  • 2
    • 0001031687 scopus 로고
    • When radicals of type 1 are generated from iodides, the hydrogen translocation (2 → 3) does not occur; instead, intermolecular halogen transfer takes place: Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333.
    • (1995) J. Org. Chem. , vol.60 , pp. 8332-8333
    • Martinez-Grau, A.1    Curran, D.P.2
  • 6
    • 0029995559 scopus 로고    scopus 로고
    • For recent examples involving carbon radicals, see: (a) Bogen, S.; Malacria, M. J. Am. Chem. Soc. 1996, 118, 3992-3993.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3992-3993
    • Bogen, S.1    Malacria, M.2
  • 11
    • 0001312951 scopus 로고
    • (f) Schultz, A. G.; Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8044-8050. Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 1029-1040.
    • (1995) J. Org. Chem. , vol.60 , pp. 8044-8050
    • Schultz, A.G.1    Guzzo, P.R.2    Nowak, D.M.3
  • 14
    • 0004278145 scopus 로고
    • Wiley: New York
    • The designation "Corey lactone" has been used in recent literature to refer to a variety of hydroxyl-protected derivatives of the hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one system. Reviews on prostaglandin synthesis: (a) Mitra, A. The Synthesis of Prostaglandins; Wiley: New York, 1977.
    • (1977) The Synthesis of Prostaglandins
    • Mitra, A.1
  • 17
    • 84913975349 scopus 로고
    • (a) Wohl, A. Chem. Ber. 1908, 41, 3599-3612.
    • (1908) Chem. Ber. , vol.41 , pp. 3599-3612
    • Wohl, A.1
  • 23
    • 0345051516 scopus 로고    scopus 로고
    • note
    • 2NEt) of the resulting alcohol gave an olefin that could be hydroborated only in yields of <40%, and so this approach was abandoned.
  • 24
    • 19044368052 scopus 로고
    • and references therein
    • Koreeda, M.; Wu, J. Synlett 1995, 850-852, and references therein.
    • (1995) Synlett , pp. 850-852
    • Koreeda, M.1    Wu, J.2
  • 27
    • 0029151342 scopus 로고
    • (b) For spectral data on the C(4) epimer, see: Zanoni, G.; Vidari, G. J. Org. Chem. 1995, 60, 5319-5323.
    • (1995) J. Org. Chem. , vol.60 , pp. 5319-5323
    • Zanoni, G.1    Vidari, G.2
  • 28
    • 0344189234 scopus 로고    scopus 로고
    • note
    • 3, MeOH) of the acetate (spontaneous lactonization occurred; 48% from the aldehyde).
  • 31
    • 0344620888 scopus 로고    scopus 로고
    • The use of TBAF in this step resulted in complete decomposition of the starting material
    • The use of TBAF in this step resulted in complete decomposition of the starting material.
  • 32
    • 0344620887 scopus 로고    scopus 로고
    • The isomeric ketal was isolated in 6% yield
    • The isomeric ketal was isolated in 6% yield.
  • 36
    • 0345483122 scopus 로고    scopus 로고
    • note
    • -1).
  • 37
    • 0344620886 scopus 로고    scopus 로고
    • note
    • 2SiCl) might have made it react with high selectivity.
  • 38
    • 0028283367 scopus 로고
    • The anomeric configuration was established by a TROESY NMR (600 MHz) experiment that established the stereochemistry of 41α. (27) Cf. (a) Serra, C.; Dewynter, G.; Montero, J.-L.; Imbach, J.-L. Tetrahedron 1994, 50, 8427-8444.
    • (1994) Tetrahedron , vol.50 , pp. 8427-8444
    • Serra, C.1    Dewynter, G.2    Montero, J.-L.3    Imbach, J.-L.4
  • 47
    • 0030872601 scopus 로고    scopus 로고
    • (b) See also: Koda, Y. Physiol. Plant. 1997, 100, 639-646.
    • (1997) Physiol. Plant. , vol.100 , pp. 639-646
    • Koda, Y.1
  • 63
    • 0344620881 scopus 로고    scopus 로고
    • A methoxymethyl group is unsuitable, as it cannot be removed in a satisfactory manner in the penultimate step of the synthesis of methyl epi-jasmonate (cf. ref 9)
    • A methoxymethyl group is unsuitable, as it cannot be removed in a satisfactory manner in the penultimate step of the synthesis of methyl epi-jasmonate (cf. ref 9).
  • 64
    • 0344620880 scopus 로고    scopus 로고
    • We had initially assumed that deprotonation of esters 16, followed by kinetic reprotonation, would afford an all-syn trisubstituted cyclopentane system, but we were unable to modify the stereochemistry in this way, and the task was accomplished by the indirect method described
    • We had initially assumed that deprotonation of esters 16, followed by kinetic reprotonation, would afford an all-syn trisubstituted cyclopentane system, but we were unable to modify the stereochemistry in this way, and the task was accomplished by the indirect method described.
  • 65
    • 0344620879 scopus 로고    scopus 로고
    • The final oxidation step is best done with PDC (see refs 32c and 32f) or PCC (see ref 32e)
    • The final oxidation step is best done with PDC (see refs 32c and 32f) or PCC (see ref 32e).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.