1981
DOI: 10.1021/jo00320a028
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of 7,9-di-O-methyl-11-oxosibiromycinone

Abstract: The synthesis of 7,9-di-O-methyl-ll-oxosibiromycinone (8) is described. Nitration of methyl 4-methyl-3,5dimethoxybenzoate (18) gave the corresponding nitro derivative 20 which was converted to 4-methyl-3,5-dimethoxy-2-nitrobenzoyl chloride (24). Ethyl 4-formylpyrrole-2-carboxylate (10) was treated with ethylmagnesium bromide and the resulting secondary alcohol 25 heated in dimethyl sulfoxide to afford ethyl (£)-4-(lpropenyl)pyrrole-2-carboxylate (26). Amide bond formation between acid chloride 24 and the sodiu… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

1
14
0

Year Published

1981
1981
2023
2023

Publication Types

Select...
8
1
1

Relationship

0
10

Authors

Journals

citations
Cited by 38 publications
(20 citation statements)
references
References 0 publications
1
14
0
Order By: Relevance
“…The π electron number contributes to its aromaticity, which can also be reflected by the resonance energy. The resonance energy values of benzene, naphthalene, and phenanthrene are 152, 255, and 381 kcal/mol, 24 respectively, which are consistent with the order of their π electron numbers. Similar to thiophenic sulfur compounds, 2-MNap shows a higher adsorption selectivity than Nap, which may be attributed to the electron donation from the methyl group bonded to the aromatic system of 2-MNap.…”
Section: Discussionsupporting
confidence: 66%
“…The π electron number contributes to its aromaticity, which can also be reflected by the resonance energy. The resonance energy values of benzene, naphthalene, and phenanthrene are 152, 255, and 381 kcal/mol, 24 respectively, which are consistent with the order of their π electron numbers. Similar to thiophenic sulfur compounds, 2-MNap shows a higher adsorption selectivity than Nap, which may be attributed to the electron donation from the methyl group bonded to the aromatic system of 2-MNap.…”
Section: Discussionsupporting
confidence: 66%
“…Carboxylate groups quickly revert to the parallel position as restraints are released. There is an appreciable energy barrier that prevents rotation of carboxylate groups attached to phenyl rings because the group extends the system’s π conjugation (see Figure S30 of the Supporting Information), which is significant even considering possible overestimates of the barrier height in the classical force field.…”
Section: Results and Discussionmentioning
confidence: 98%
“…21 Since HDI does not form a protective layer with an EC-based electrolyte under the same conditions, we tend to attribute this difference to the absence of methyl protection, 19b,22 which reduces the nucleophilicity of positive charge and lowers the reactivity with the isocyanate group. 23 The resistances of electrodes aer 4.6 V(vs. Li/Li + ) -3 h polarization are tested on a semiconductor parameter analyzer. Since the probe for the conductivity test is 50 nm, this measurement should reveal the variation of mono-particle's resistance.…”
mentioning
confidence: 99%