volume 68 issue 16 pages 6437-6439

First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2

Publication typeJournal Article
Publication date2003-07-03
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
PubMed ID:  12895084
Organic Chemistry
Abstract
Enantioselective synthesis of natural PGJ(2) has been accomplished for the first time starting from the commercially available enantiopure aldehyde 7 in 10% overall yield. The key reaction was a novel prostaglandin class interconversion, i.e., an allylic 1,3-transposition across alcohol 9 derived from compound 14 in 73% overall yield. In principle, the unnatural enantiomer of PGJ(2) could be obtained starting from the commercially available enantiopure monobenzoate 7a following our strategy.
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GOST Copy
Zanoni G. et al. First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2 // Journal of Organic Chemistry. 2003. Vol. 68. No. 16. pp. 6437-6439.
GOST all authors (up to 50) Copy
Zanoni G., Porta A., De Toma Q., Castronovo F., Vidari G. First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2 // Journal of Organic Chemistry. 2003. Vol. 68. No. 16. pp. 6437-6439.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/jo034502h
UR - https://doi.org/10.1021/jo034502h
TI - First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2
T2 - Journal of Organic Chemistry
AU - Zanoni, Giuseppe
AU - Porta, Alessio
AU - De Toma, Quintino
AU - Castronovo, Francesca
AU - Vidari, G.
PY - 2003
DA - 2003/07/03
PB - American Chemical Society (ACS)
SP - 6437-6439
IS - 16
VL - 68
PMID - 12895084
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2003_Zanoni,
author = {Giuseppe Zanoni and Alessio Porta and Quintino De Toma and Francesca Castronovo and G. Vidari},
title = {First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jo034502h},
number = {16},
pages = {6437--6439},
doi = {10.1021/jo034502h}
}
MLA
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MLA Copy
Zanoni, Giuseppe, et al. “First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2.” Journal of Organic Chemistry, vol. 68, no. 16, Jul. 2003, pp. 6437-6439. https://doi.org/10.1021/jo034502h.