Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues
Publication type: Journal Article
Publication date: 2006-04-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Palladium-catalyzed reaction of TBS ether of 4-cyclopentene-1,3-diol monoacetate (>95% ee) with an anion derived from methyl malonate and a base such as t -BuOK and LDA proceeded highly efficiently and reproducibly. The product obtained in >90% isolated yield was transformed in five steps into the key cyclopentenone possessing the α-chain at the γ position. Aldol reaction of this enone with the ω-chain aldehyde afforded the aldol adduct, and exposure of the derived mesylate to Al 2 O 3 furnished the cross-conjugated dienone of the full structure. Finally, functional group manipulation furnished Δ 12 -PGJ 2 efficiently. Similarly, 15-deoxy-Δ 12,14 -PGJ 2 , 5,6-acetylene analogues, and a 5,6-dihydro analogue were synthesized.
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Acharya H. P., Kobayashi Y. Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues // Tetrahedron. 2006. Vol. 62. No. 14. pp. 3329-3343.
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Acharya H. P., Kobayashi Y. Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues // Tetrahedron. 2006. Vol. 62. No. 14. pp. 3329-3343.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tet.2006.01.051
UR - https://doi.org/10.1016/j.tet.2006.01.051
TI - Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues
T2 - Tetrahedron
AU - Acharya, Hukum P.
AU - Kobayashi, yuichi
PY - 2006
DA - 2006/04/01
PB - Elsevier
SP - 3329-3343
IS - 14
VL - 62
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2006_Acharya,
author = {Hukum P. Acharya and yuichi Kobayashi},
title = {Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues},
journal = {Tetrahedron},
year = {2006},
volume = {62},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/j.tet.2006.01.051},
number = {14},
pages = {3329--3343},
doi = {10.1016/j.tet.2006.01.051}
}
Cite this
MLA
Copy
Acharya, Hukum P., et al. “Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues.” Tetrahedron, vol. 62, no. 14, Apr. 2006, pp. 3329-3343. https://doi.org/10.1016/j.tet.2006.01.051.