Elsevier
Tetrahedron
,  том 55 ,  издание 52 ,  страницы 15127-15140

Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides

Тип публикации: Journal Article
Дата публикации: 1999-12-01
Elsevier
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
The acyl endoperoxide arteannuin H, recently reported as a novel natural product from Artemtsia annua , has been obtained in two steps from the photooxidation of dihydroartemisinic acid, thereby confirming biogenetic speculation regarding its derivation from a secondary allylic hydroperoxide. The little studied 3,2-rearrangement reaction of such allylic hydroperoxides is also discussed. The acyl endoperoxide arteannuin H ( 4 ), recently reported as a novel natural product from Artemisia annua , has been obtained from photooxidation of dihydroartemisinic acid ( 2 ), yielding secondary allylic hydroperoxide ( 5 ). An alternative rearrangement reaction of such secondary allylic hydroperoxides, yielding for example primary allylic hydroperoxide 8 , is also discussed.
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Sy L., Ngo K. S., Brown G. D. Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides // Tetrahedron. 1999. Vol. 55. No. 52. pp. 15127-15140.
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Sy L., Ngo K. S., Brown G. D. Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides // Tetrahedron. 1999. Vol. 55. No. 52. pp. 15127-15140.
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TY - JOUR
DO - 10.1016/S0040-4020(99)00987-4
UR - https://doi.org/10.1016/S0040-4020(99)00987-4
TI - Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides
T2 - Tetrahedron
AU - Sy, Lai-King
AU - Ngo, Koon Sin
AU - Brown, Geoffrey D
PY - 1999
DA - 1999/12/01
PB - Elsevier
SP - 15127-15140
IS - 52
VL - 55
SN - 0040-4020
SN - 1464-5416
ER -
BibTex |
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@article{1999_Sy,
author = {Lai-King Sy and Koon Sin Ngo and Geoffrey D Brown},
title = {Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides},
journal = {Tetrahedron},
year = {1999},
volume = {55},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/S0040-4020(99)00987-4},
number = {52},
pages = {15127--15140},
doi = {10.1016/S0040-4020(99)00987-4}
}
MLA
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Sy, Lai-King, et al. “Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides.” Tetrahedron, vol. 55, no. 52, Dec. 1999, pp. 15127-15140. https://doi.org/10.1016/S0040-4020(99)00987-4.