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Mendeleev Communications, 2023, Volume 33, Issue 4, Pages 479–480
DOI: https://doi.org/10.1016/j.mencom.2023.06.012
(Mi mendc433)
 

This article is cited in 1 scientific paper (total in 1 paper)

Communications

A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester

Z. R. Makaev, N. S. Vostrikov, N. K. Selezneva, M. S. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
Full-text PDF (209 kB) Citations (1)
Abstract: A simple and facile synthesis of racemic 15-deoxy-Δ12,14-prostaglandin J2 methyl ester from readily available Corey lactone diol in total eleven steps was suggested. The standard methods provided a pathway to a block with an integrated w w w-chain and further to PGJ2 methyl ester. The latter was smoothly converted to the target prostaglandin in the TsOH–CH2Cl2 medium when allylic alcohol moiety was transformed to exocyclic diene substituent conjugated with endocyclic enone system.
Keywords: Corey lactone diol, prostaglandin J2 methyl ester, 15-deoxyΔ12,14-prostaglandin J2, diastereoselective reaction, dehydration, dienes.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (6.4 Mb)


Citation: Z. R. Makaev, N. S. Vostrikov, N. K. Selezneva, M. S. Miftakhov, “A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester”, Mendeleev Commun., 33:4 (2023), 479–480
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  • https://www.mathnet.ru/eng/mendc/v33/i4/p479
  • This publication is cited in the following 1 articles:
    1. A. A. Vasil'ev, G. M. Zhdankina, S. G. Zlotin, “Simple synthesis of erythro-2,3,6-trimethylhepta-4,6-dien-1-ol acetate, a lasiol precursor”, Russ Chem Bull, 73:5 (2024), 1465  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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