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Volumn 121, Issue 43, 1999, Pages 10012-10020

Total synthesis of clavepictines A and B. Diastereoselective cyclization of δ-aminoallenes

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CLAVEPICTINE A; CLAVEPICTINE B; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0000490780     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9925958     Document Type: Article
Times cited : (96)

References (88)
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    • (1983) Tetrahedron Lett. , vol.24 , pp. 1719
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    • (1987) Tetrahedron Lett. , vol.28 , pp. 1529
    • Tominaga, Y.1    Kohra, S.2    Hosomi, A.3
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    • (1989) J. Chem. Soc., Perkin Trans. 1 , pp. 1211
    • Takahata, H.1    Takahashi, K.2    Wang, E.-C.3    Yamazaki, T.4
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    • (1984) J. Org. Chem. , vol.49 , pp. 4397
    • Zezza, C.A.1    Smith, M.B.2    Ross, B.A.3    Arhin, A.4    Cronin, P.L.E.5
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    • note
    • The carbamates 8 and 9 and related compounds all adopt a conformation in which the methyl group is axial to avoid allylic strain.
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    • For cyclization of allenes bearing a proximate nitrogen nucleophile, see: (a) Prasad, J. S.; Liebeskind, L. S. Tetrahedron Lett. 1988, 29, 4253. (b) Arseniyadis, S.; Gore, J. Tetrahedron Lett. 1983, 24, 3997. (c) Arseniyadis, S.; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729. (d) Lathbury, D.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1986, 114. (e) Kinsman, R.; Lathbury, D.; Vernon, P.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1987, 243. (f) Shaw, R. W.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1994, 3549.
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    • +-mediated cyclopentenone annulation: (a) Balme, G.; Malacria, M.; Goré, J. Tetrahedron Lett. 1979, 7. (b) Malacria, M.; Goré, J. J. Org. Chem. 1979, 44, 885. (c) Dulcere, J. P.; Grimaldi, J.; Santelli, M. Tetrahedron Lett. 1981, 22, 3179. (d) Kim, S. J.; Cha, J. K. Tetrahedron Lett. 1988, 29, 5613 and references therein.
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    • and references therein
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    • note
    • 3 (0.3 equiv) in aqueous acetone, a δ-amino allenyl alkyne underwent cyclization without complication.
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    • Oxford University Press: Oxford, UK
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    • Yields given in Scheme 14 are based on recovered starting triflate (13-18%)
    • Yields given in Scheme 14 are based on recovered starting triflate (13-18%).
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    • Reference 7b
    • (a) Reference 7b.
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    • note
    • (b) Use of the allylic o-nitrobenzeneselenoxide resulted in the [2,3]-sigmatropic rearrangement to provide the 1,3-transposed allylic alcohol. Lability of allylic selenoxides, even in the absence of trapping agents other than adventitious moisture, was previously noted by Reich.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.