2003
DOI: 10.1081/scc-120018690
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of Antibiotic Stilbenes by Reductive Metalation of 3,4,5-Trimethoxybenzaldehyde Dimethyl Acetal

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1

Citation Types

0
6
0

Year Published

2003
2003
2022
2022

Publication Types

Select...
8

Relationship

1
7

Authors

Journals

citations
Cited by 9 publications
(6 citation statements)
references
References 16 publications
0
6
0
Order By: Relevance
“…3,5,6-Trimethylpyrazine-2-carbaldehyde 6 was prepared by the Pfitzner-Moffatt oxidation [20]. The intermediate 5 or 6 was converted to stilbene derivatives (A1-27) via Horner-Wadsworth-Emmons reaction [21]. The chemical structures of newly synthesized compounds were confirmed by IR, NMR, and ESI-MS.…”
Section: Resultsmentioning
confidence: 99%
“…3,5,6-Trimethylpyrazine-2-carbaldehyde 6 was prepared by the Pfitzner-Moffatt oxidation [20]. The intermediate 5 or 6 was converted to stilbene derivatives (A1-27) via Horner-Wadsworth-Emmons reaction [21]. The chemical structures of newly synthesized compounds were confirmed by IR, NMR, and ESI-MS.…”
Section: Resultsmentioning
confidence: 99%
“…Acetal a was then subjected to a reductive metalation and alkylation to selectively replace the 4-methoxy group with an ethyl substituent. 45 After regeneration of the aldehyde moiety ( b ), oxidation with Oxone afforded carboxylic acid c , the structure of which was confirmed by X-ray crystallography. 46 Subsequent demethylation with boron tribromide gave d , which was smoothly reduced to the benzyl alcohol e by reaction with borane-dimethyl sulfide complex.…”
Section: Resultsmentioning
confidence: 89%
“…The molecule 9a had been obtained from 1 by Heck vinylation using 1-octene followed by a reduction of the double bond. 26 The porphyrin synthesis was made under modified Lindsey conditions. 27,28 The porphyrin 9a was then converted into the oxonaphthoporphyrin 10a via the Friedel-Crafts reaction sequence described by Callot.…”
Section: Synthesis Of Alkyl Substituted Oxonaphthoporphyrins (10a 10b)mentioning
confidence: 99%