Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone
Тип публикации: Journal Article
Дата публикации: 1991-01-01
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
Several 2-phenylsulphonyl-piperidines and -pyrrolidines were prepared from the corresponding N-acyl aminals by treatment with benzenesulphinic acid. On reaction with various carbon nucleophiles these sulphones gave good yields of substitution products. Typical nucleophiles used in these studies were organometallic reagents derived from Grignard reagents and zinc halide together with silyl enol ethers, silyl ketene acetals, allylsilanes and trimethylsilyl cyanide in the presence of a Lewis acid. These methods were employed in the synthesis of two natural product alkaloids; Norruspoline (38) and Ruspolinone (40). Several 2-phenylsulphonyl-piperidines and -pyrrolidines were prepared from the corresponding N -acyl aminals by treatment with PhSO 2 H. On reaction with various carbon nucleophiles these sulphones gave good yields of substitution products. These methods were employed in the synthesis of two natural product alkaloids; Norruspoline and Ruspolinone.
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Brown D. S. et al. Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone // Tetrahedron. 1991. Vol. 47. No. 7. pp. 1311-1328.
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Brown D. S., Charreau P., Hansson T., Ley S. V. Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone // Tetrahedron. 1991. Vol. 47. No. 7. pp. 1311-1328.
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TY - JOUR
DO - 10.1016/S0040-4020(01)86388-2
UR - https://doi.org/10.1016/S0040-4020(01)86388-2
TI - Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone
T2 - Tetrahedron
AU - Brown, Dearg S.
AU - Charreau, Philippe
AU - Hansson, Thomas
AU - Ley, S V
PY - 1991
DA - 1991/01/01
PB - Elsevier
SP - 1311-1328
IS - 7
VL - 47
SN - 0040-4020
SN - 1464-5416
ER -
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@article{1991_Brown,
author = {Dearg S. Brown and Philippe Charreau and Thomas Hansson and S V Ley},
title = {Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone},
journal = {Tetrahedron},
year = {1991},
volume = {47},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0040-4020(01)86388-2},
number = {7},
pages = {1311--1328},
doi = {10.1016/S0040-4020(01)86388-2}
}
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MLA
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Brown, Dearg S., et al. “Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone.” Tetrahedron, vol. 47, no. 7, Jan. 1991, pp. 1311-1328. https://doi.org/10.1016/S0040-4020(01)86388-2.