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Volumn 5, Issue 12, 2003, Pages 2181-2184

New strategy for the synthesis of tetrahydroisoquinoline alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; LACTAM; ORGANOLITHIUM COMPOUND; SULFONIUM DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE;

EID: 0141630547     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034683+     Document Type: Article
Times cited : (68)

References (28)
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    • Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. In this paper, the yield of 3-hydroxymethylisoquinoline was 0% when propargyl alcohol was used (Table 3, entry 5 in the above reference). Simply using protected derivatives as in Scheme 3 works well.
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    • note
    • Enantiomers were separated using chiral HPLC.
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    • Closest analogy to the type of reaction is the intramolecular Schmidt rearrangement. (a) Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449. (b) Mossman, C. J.; Aubé, J. Tetrahedron 1996, 52, 3403.
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    • Closest analogy to the type of reaction is the intramolecular Schmidt rearrangement. (a) Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449. (b) Mossman, C. J.; Aubé, J. Tetrahedron 1996, 52, 3403.
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