Synthesis of bicyclic α-methylene-γ-lactones involving stereocontrolled introduction of an homoallylic acyloxy group

1976 ◽  
pp. 584-585
Author(s):  
S. Mubarik Ali ◽  
Stanley M. Roberts
Keyword(s):  
Acyloxy Group

Combinatorial Synthesis of Novel 1-Sulfonyloxy/acyloxyeugenol Derivatives as Fungicidal Agents

2021 ◽  
Vol 24 ◽  
Author(s):  
Genqiang Chen ◽  
Lina Zhu ◽  
Jiaxuan He ◽  
Song Zhang ◽  
Yuanhao Li ◽  
...  
Keyword(s):  
Fungicidal Activity ◽  
High Efficiency ◽  
Biological Activities ◽  
Phytophthora Capsici ◽  
Effective Control ◽  
Syzygium Aromaticum ◽  
Wide Range ◽  
Structural Skeleton ◽  
Acyloxy Group

Background: Developing the high-efficiency and low-risk small-molecule green-fungicide is the key to effective control of the plant pathogenic oomycetes. Essential oils play a very important role in novel fungicide discovery for their unique sources and potential target sites. Eugenol, a kind of plant essential oil, was mainly isolated from the unopened and dried flower buds of Syzygium aromaticum of the Myrtaceae family. Due to its unique structural skeleton, eugenol and its derivatives have exhibited a wide range of biological activities. However, study on the synthesis of novel 1-sulfonyloxy/acyloxyeugenol derivatives as fungicidal agents against Phytophthora capsici has not yet been reported. Methods: Twenty-six novel 1-sulfonyloxy/acyloxyeugenol derivatives (3a-p and 5a-j) were prepared and their structures were well characterized by 1H NMR, HRMS, and m.p.. Their fungicidal activity was evaluated against P. capsici by using the mycelial growth rate method. Results: To find novel natural-product-based fungicidal agents to control the plant pathogenic oomycetes, we herein designed and synthesized two series of novel 1-sulfonyloxy/acyloxyeugenol derivatives (3a-p and 5a-j) as fungicidal agents against P. capsici Leonian, in vitro. Results of fungicidal activity revealed that, among all compounds, especially compounds 3a, 3f, and 3n displayed the most potent anti-oomycete activity against P. capsici with EC50 values of 79.05, 75.05, and 70.80, respectively. Conclusion: The results revealed that the anti-oomycete activity of eugenol with the sulfonyloxy group was higher than that with the acyloxy group. It is suggested that the fungicidal activity of eugenol can be improved by introducing the sulfonyloxy group. This will pave the way for further design, structural modification, and to develop eugenol derivatives as fungicidal agents.

scholarly journals The Cyclic Nitronate Route to Pharmaceutical Molecules: Synthesis of GSK’s Potent PDE4 Inhibitor as a Case Study

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3613
Author(s):  
Evgeny V. Pospelov ◽  
Ivan S. Golovanov ◽  
Sema L. Ioffe ◽  
Alexey Yu. Sukhorukov
Keyword(s):  
Density Functional ◽  
Sigmatropic Rearrangement ◽  
Pde4 Inhibitor ◽  
Straightforward Manner ◽  
Functional Theory ◽  
Oxazine Ring ◽  
Anchimeric Assistance ◽  
Pharmaceutical Molecules ◽  
Acyloxy Group

An efficient asymmetric synthesis of GlaxoSmithKline’s potent PDE4 inhibitor was accomplished in eight steps from a catechol-derived nitroalkene. The key intermediate (3-acyloxymethyl-substituted 1,2-oxazine) was prepared in a straightforward manner by tandem acylation/(3,3)-sigmatropic rearrangement of the corresponding 1,2-oxazine-N-oxide. The latter was assembled by a (4 + 2)-cycloaddition between the suitably substituted nitroalkene and vinyl ether. Facile acetal epimerization at the C-6 position in 1,2-oxazine ring was observed in the course of reduction with NaBH3CN in AcOH. Density functional theory (DFT) calculations suggest that the epimerization may proceed through an unusual tricyclic oxazolo(1,2)oxazinium cation formed via double anchimeric assistance from a distant acyloxy group and the nitrogen atom of the 1,2-oxazine ring.

DISPLACEMENT OF A NITRO GROUP BY AN ACYLOXY GROUP UNDER FRIEDEL-CRAFTS CONDITIONS

1964 ◽  
pp. 275-283
Author(s):  
P.K. BHATTACHARYYA ◽  
A.C. GHOSH ◽  
V.M. SATHE ◽  
N.L. DUTTA ◽  
MANSA RAM
Keyword(s):  
Nitro Group ◽  
Acyloxy Group

Geminal Systems. Part 51. Acyloxy Group Exchange in N-Acyloxy-N-alkoxyamides.

ChemInform ◽  
2005 ◽  
Vol 36 (8) ◽  
Author(s):  
Vasiliy G. Shtamburg ◽  
Alexandr V. Tsygankov ◽  
Evgeniy Klots ◽  
Remir G. Kostyanovsky
Keyword(s):  
Acyloxy Group

Synthesis of Phenanthroindolizidine Alkaloids with an Acyloxy Group at the C3 Position and their Antitumor Activities and Toxicities

2012 ◽  
Vol 9 (5) ◽  
pp. 447-453 ◽  
Author(s):  
Takashi Ikeda ◽  
Takashi Yaegashi ◽  
Takeshi Matsuzaki ◽  
Ryuta Yamazaki ◽  
Satoshi Ueno ◽  
...  
Keyword(s):  
Antitumor Activities ◽  
Phenanthroindolizidine Alkaloids ◽  
Acyloxy Group
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