A concise synthesis of the methyl esters of (10S)-hepoxilin B3 and (10S)-trioxilin B3
Тип публикации: Journal Article
Дата публикации: 1993-05-01
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Краткое описание
2,3:4,5-Di-O-Isopropylidene-D-mannose was converted to lactol 2,3-O-isopropylidene-6(Z)-dodecene-L-ribofuranose (6) by Grignard addition with propargyl magnesium bromide, alkylation of the resulting terminal alkyne, partial hydrogenation of the triple bond, and finally chemoselective cleavage of the 1,2-O-isopropylidene and subsequent periodate cleavage of the glycol. Wittig olefination of 6 led to methyl 10(S),11(R)-O-isopropylidene-10,11,12(R)-trihydroxyeicosa-5,8,14(Z)-trienoate (5), which could be converted to (10S)-trioxilin B 3 methyl ester (3) in one step or to (10S)-hepoxilin B 3 methyl ester (4) in three steps
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Wu W., Wu Y. A concise synthesis of the methyl esters of (10S)-hepoxilin B3 and (10S)-trioxilin B3 // Journal of Organic Chemistry. 1993. Vol. 58. No. 10. pp. 2760-2762.
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Wu W., Wu Y. A concise synthesis of the methyl esters of (10S)-hepoxilin B3 and (10S)-trioxilin B3 // Journal of Organic Chemistry. 1993. Vol. 58. No. 10. pp. 2760-2762.
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TY - JOUR
DO - 10.1021/jo00062a017
UR - https://doi.org/10.1021/jo00062a017
TI - A concise synthesis of the methyl esters of (10S)-hepoxilin B3 and (10S)-trioxilin B3
T2 - Journal of Organic Chemistry
AU - Wu, Wenlian
AU - Wu, Yulin
PY - 1993
DA - 1993/05/01
PB - American Chemical Society (ACS)
SP - 2760-2762
IS - 10
VL - 58
SN - 0022-3263
SN - 1520-6904
ER -
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@article{1993_Wu,
author = {Wenlian Wu and Yulin Wu},
title = {A concise synthesis of the methyl esters of (10S)-hepoxilin B3 and (10S)-trioxilin B3},
journal = {Journal of Organic Chemistry},
year = {1993},
volume = {58},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jo00062a017},
number = {10},
pages = {2760--2762},
doi = {10.1021/jo00062a017}
}
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MLA
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Wu, Wenlian, and Yulin Wu. “A concise synthesis of the methyl esters of (10S)-hepoxilin B3 and (10S)-trioxilin B3.” Journal of Organic Chemistry, vol. 58, no. 10, May. 1993, pp. 2760-2762. https://doi.org/10.1021/jo00062a017.