Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (−)-isoretronecanol and (+)-laburnine
Publication type: Journal Article
Publication date: 1999-04-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The adducts of a stereoselective radical addition of tertiary amines with (5 R )-5-menthyloxy-2[5 H ]-furanone were transformed very efficiently into enantiomerically pure pyrrolizidine and indolizidine alkaloids, through a three steps sequence. In a radical reaction, tertiary amines are added to (5 R )-5-menthyloxy-2[5 H ]-furanone 1 . The adducts are transformed in few steps into (−)-isoretronecanol 2 and (+)-laburnine 3 .
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Bertrand S. et al. Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (−)-isoretronecanol and (+)-laburnine // Tetrahedron Letters. 1999. Vol. 40. No. 16. pp. 3173-3174.
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Bertrand S., Hoffmann N., Pete J. Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (−)-isoretronecanol and (+)-laburnine // Tetrahedron Letters. 1999. Vol. 40. No. 16. pp. 3173-3174.
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TY - JOUR
DO - 10.1016/S0040-4039(99)00452-9
UR - https://doi.org/10.1016/S0040-4039(99)00452-9
TI - Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (−)-isoretronecanol and (+)-laburnine
T2 - Tetrahedron Letters
AU - Bertrand, Samuel
AU - Hoffmann, Norbert
AU - Pete, Jean-Pierre
PY - 1999
DA - 1999/04/01
PB - Elsevier
SP - 3173-3174
IS - 16
VL - 40
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{1999_Bertrand,
author = {Samuel Bertrand and Norbert Hoffmann and Jean-Pierre Pete},
title = {Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (−)-isoretronecanol and (+)-laburnine},
journal = {Tetrahedron Letters},
year = {1999},
volume = {40},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/S0040-4039(99)00452-9},
number = {16},
pages = {3173--3174},
doi = {10.1016/S0040-4039(99)00452-9}
}
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MLA
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Bertrand, Samuel, et al. “Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (−)-isoretronecanol and (+)-laburnine.” Tetrahedron Letters, vol. 40, no. 16, Apr. 1999, pp. 3173-3174. https://doi.org/10.1016/S0040-4039(99)00452-9.