Asymmetric Total Synthesis of Eupalinilide E, a Promoter of Human HSPC Expansion
Publication type: Journal Article
Publication date: 2022-06-28
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
35763266
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A concise and scalable asymmetric total synthesis of eupalinilde E from (R)-(-)-carvone in 12 steps is reported with an overall yield of 20%. The key steps of the synthesis are a tandem Favorskii rearrangement-elimination reaction in the chromatography-free synthesis of carvone-derived 2-cyclopentene carbaldehyde and its catalyst-free stereospecific tandem allylboration-lactonization using recyclable trifluoroethanol as a promoter and solvent affording β-hydroxymethyl-α-methylene-γ-butyrolactone.
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Metrics
14
Total citations:
14
Citations from 2024:
7
(50%)
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GOST
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Maity R., Hajra S. Asymmetric Total Synthesis of Eupalinilide E, a Promoter of Human HSPC Expansion // Organic Letters. 2022. Vol. 24. No. 26. pp. 4745-4749.
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Maity R., Hajra S. Asymmetric Total Synthesis of Eupalinilide E, a Promoter of Human HSPC Expansion // Organic Letters. 2022. Vol. 24. No. 26. pp. 4745-4749.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.2c01684
UR - https://doi.org/10.1021/acs.orglett.2c01684
TI - Asymmetric Total Synthesis of Eupalinilide E, a Promoter of Human HSPC Expansion
T2 - Organic Letters
AU - Maity, Ramkrishna
AU - Hajra, Saumen
PY - 2022
DA - 2022/06/28
PB - American Chemical Society (ACS)
SP - 4745-4749
IS - 26
VL - 24
PMID - 35763266
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2022_Maity,
author = {Ramkrishna Maity and Saumen Hajra},
title = {Asymmetric Total Synthesis of Eupalinilide E, a Promoter of Human HSPC Expansion},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.2c01684},
number = {26},
pages = {4745--4749},
doi = {10.1021/acs.orglett.2c01684}
}
Cite this
MLA
Copy
Maity, Ramkrishna, and Saumen Hajra. “Asymmetric Total Synthesis of Eupalinilide E, a Promoter of Human HSPC Expansion.” Organic Letters, vol. 24, no. 26, Jun. 2022, pp. 4745-4749. https://doi.org/10.1021/acs.orglett.2c01684.