Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds
Publication type: Journal Article
Publication date: 2004-02-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A key cyclopentenone possessing the α-chain was synthesized from TBS ether of 4-cyclopentene-1,3-diol monoacetate, and submitted to aldol reaction at the α ′ -position with the ω-chain aldehydes followed by dehydration to produce the title compounds. In a similar manner, 5-dehydro compounds (acetylene analogues) were synthesized successfully. In addition, palladium-catalyzed reaction of 4-cyclopentene-1,3-diol monoacetate with methyl malonate, the first step of the synthesis, was improved to afford the product in high yield by using t -BuOK or LDA in place of NaH.
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Acharya H. P., Kobayashi Y. Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds // Tetrahedron Letters. 2004. Vol. 45. No. 6. pp. 1199-1202.
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Acharya H. P., Kobayashi Y. Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds // Tetrahedron Letters. 2004. Vol. 45. No. 6. pp. 1199-1202.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tetlet.2003.11.143
UR - https://doi.org/10.1016/j.tetlet.2003.11.143
TI - Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds
T2 - Tetrahedron Letters
AU - Acharya, Hukum P.
AU - Kobayashi, yuichi
PY - 2004
DA - 2004/02/01
PB - Elsevier
SP - 1199-1202
IS - 6
VL - 45
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2004_Acharya,
author = {Hukum P. Acharya and yuichi Kobayashi},
title = {Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds},
journal = {Tetrahedron Letters},
year = {2004},
volume = {45},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.tetlet.2003.11.143},
number = {6},
pages = {1199--1202},
doi = {10.1016/j.tetlet.2003.11.143}
}
Cite this
MLA
Copy
Acharya, Hukum P., and yuichi Kobayashi. “Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds.” Tetrahedron Letters, vol. 45, no. 6, Feb. 2004, pp. 1199-1202. https://doi.org/10.1016/j.tetlet.2003.11.143.