Enantioselective Total Syntheses of (-)-Isonitramine, (-)-Sibirine, and (+)-Nitramine by Ring-Closing Metathesis
Publication type: Journal Article
Publication date: 2011-10-31
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Concise enantioselective total syntheses of naturally occurring 2-azaspiro[5,5]undecan-7-ol (Nitraria) alkaloids viz. (–)-isonitramine, (–)-sibirine, and (+)-nitramine are accomplished in 42, 38, and 25 % overall yield, respectively, in six steps starting from enantiomerically pure (S)-methyl 3-allyl-2-oxo-1,2,3,6-tetrahydropyridine-3-carboxylate (>99 % ee). The key feature of the syntheses involves diastereoselective Hosomi–Sakurai allylation followed by ring-closing metathesis.
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17
Total citations:
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Citations from 2025:
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(5.88%)
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GOST
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Pandey G. P. et al. Enantioselective Total Syntheses of (-)-Isonitramine, (-)-Sibirine, and (+)-Nitramine by Ring-Closing Metathesis // European Journal of Organic Chemistry. 2011. Vol. 2011. No. 36. pp. 7372-7377.
GOST all authors (up to 50)
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Pandey G. P., C P. K., Kumar Burugu S., Puranik V. G. Enantioselective Total Syntheses of (-)-Isonitramine, (-)-Sibirine, and (+)-Nitramine by Ring-Closing Metathesis // European Journal of Organic Chemistry. 2011. Vol. 2011. No. 36. pp. 7372-7377.
Cite this
RIS
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TY - JOUR
DO - 10.1002/ejoc.201101256
UR - https://doi.org/10.1002/ejoc.201101256
TI - Enantioselective Total Syntheses of (-)-Isonitramine, (-)-Sibirine, and (+)-Nitramine by Ring-Closing Metathesis
T2 - European Journal of Organic Chemistry
AU - Pandey, G. P.
AU - C, Prasanna Kumara
AU - Kumar Burugu, Shiva
AU - Puranik, Vedavati G.
PY - 2011
DA - 2011/10/31
PB - Wiley
SP - 7372-7377
IS - 36
VL - 2011
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
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@article{2011_Pandey,
author = {G. P. Pandey and Prasanna Kumara C and Shiva Kumar Burugu and Vedavati G. Puranik},
title = {Enantioselective Total Syntheses of (-)-Isonitramine, (-)-Sibirine, and (+)-Nitramine by Ring-Closing Metathesis},
journal = {European Journal of Organic Chemistry},
year = {2011},
volume = {2011},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/ejoc.201101256},
number = {36},
pages = {7372--7377},
doi = {10.1002/ejoc.201101256}
}
Cite this
MLA
Copy
Pandey, G. P., et al. “Enantioselective Total Syntheses of (-)-Isonitramine, (-)-Sibirine, and (+)-Nitramine by Ring-Closing Metathesis.” European Journal of Organic Chemistry, vol. 2011, no. 36, Oct. 2011, pp. 7372-7377. https://doi.org/10.1002/ejoc.201101256.