RUTHENIUM HYDRIDE-CATALYZED DOUBLE BOND MIGRATION OF 2,5-DIMETHOXY-2,5-DIHYDROFURANS. A NEW PROCESS FOR THE PREPARATION OF γ-KETOESTERS

1982 ◽  
Vol 11 (1) ◽  
pp. 23-26 ◽  
Author(s):  
Kenji Hirai ◽  
Hiroharu Suzuki ◽  
Hiroshi Kashiwagi ◽  
Yoshihiko Moro-Oka ◽  
Tsuneo Ikawa
Keyword(s):  
Double Bond ◽  
Double Bond Migration ◽  
Ruthenium Hydride ◽  
New Process

The role of the functional group in double bond migration in allylic systems catalysed by ruthenium hydride complexes

2006 ◽  
Vol 253 (1-2) ◽  
pp. 132-146 ◽  
Author(s):  
S. Krompiec ◽  
N. Kuźnik ◽  
M. Krompiec ◽  
R. Penczek ◽  
J. Mrzigod ◽  
...  
Keyword(s):  
Double Bond ◽  
Functional Group ◽  
Double Bond Migration ◽  
Ruthenium Hydride ◽  
Hydride Complexes

scholarly journals Synthesis of Dihydropyrano[3,2-c]pyrazoles via Double Bond Migration and Ring-Closing Metathesis

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 296 ◽  
Author(s):  
Yoshihide Usami ◽  
Kodai Sumimoto ◽  
Azusa Kishima ◽  
Yuya Tatsui ◽  
Hiroki Yoneyama ◽  
...  
Keyword(s):  
Double Bond ◽  
Claisen Rearrangement ◽  
Ring Closing Metathesis ◽  
Double Bond Migration ◽  
Ruthenium Hydride

Three types of pyrazole-fused heterobicycles, i.e., 1,5-, 1,7-, and 2,5-dihydropyrano[3,2-c]pyrazoles, were synthesized from 4-allyloxy-1H-pyrazoles. A sequence of the Claisen rearrangement of 4-allyloxy-1H-pyrazoles, ruthenium-hydride-catalyzed double bond migration, O-allylation, and ring-closing metathesis was employed in this study.

The Role of the Functional Group in Double Bond Migration of Allylic Systems Catalyzed by Ruthenium Hydride Complexes

ChemInform ◽  
2007 ◽  
Vol 38 (25) ◽  
Author(s):  
S. Krompiec ◽  
N. Kuznik ◽  
M. Krompiec ◽  
R. Penczek ◽  
J. Mrzigod ◽  
...  
Keyword(s):  
Double Bond ◽  
Functional Group ◽  
Double Bond Migration ◽  
Ruthenium Hydride ◽  
Hydride Complexes

Remote double bond migration via rhodium catalysis: a novel enone transposition

1976 ◽  
Vol 98 (22) ◽  
pp. 7102-7104 ◽  
Author(s):  
Paul A. Grieco ◽  
Mugio Nishizawa ◽  
Nebojsa Marinovic ◽  
William J. Ehmann
Keyword(s):  
Double Bond ◽  
Rhodium Catalysis ◽  
Double Bond Migration

ChemInform Abstract: Double-Bond Migration in Pyrano(4,3-b)pyrylium Cations.

ChemInform ◽  
2010 ◽  
Vol 25 (8) ◽  
pp. no-no
Author(s):  
F. M. DEAN ◽  
M. MALKI ◽  
L. J. O'KEEFFE
Keyword(s):  
Double Bond ◽  
Double Bond Migration

scholarly journals Oxepinamide F biosynthesis involves enzymatic d-aminoacyl epimerization, 3H-oxepin formation, and hydroxylation induced double bond migration

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Liujuan Zheng ◽  
Haowen Wang ◽  
Aili Fan ◽  
Shu-Ming Li
Keyword(s):  
Cytochrome P450 ◽  
Double Bond ◽  
Biosynthetic Pathway ◽  
Hydroxyl Group ◽  
Cytochrome P450 Enzyme ◽  
Double Bond Migration ◽  
Feeding Experiments ◽  
Aspergillus Ustus ◽  
P450 Enzyme ◽  
Derivatives Of

Abstract Oxepinamides are derivatives of anthranilyl-containing tripeptides and share an oxepin ring and a fused pyrimidinone moiety. To the best of our knowledge, no studies have been reported on the elucidation of an oxepinamide biosynthetic pathway and conversion of a quinazolinone to a pyrimidinone-fused 1H-oxepin framework by a cytochrome P450 enzyme in fungal natural product biosynthesis. Here we report the isolation of oxepinamide F from Aspergillus ustus and identification of its biosynthetic pathway by gene deletion, heterologous expression, feeding experiments, and enzyme assays. The nonribosomal peptide synthase (NRPS) OpaA assembles the quinazolinone core with d-Phe incorporation. The cytochrome P450 enzyme OpaB catalyzes alone the oxepin ring formation. The flavoenzyme OpaC installs subsequently one hydroxyl group at the oxepin ring, accompanied by double bond migration. The epimerase OpaE changes the d-Phe residue back to l-form, which is essential for the final methylation by OpaF.

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