Synthesen substituierter Butenolide

Haefliger, W.; Petrzilka, Th.

doi:10.1002/hlca.19660490632

Cited by 20 publications

(5 citation statements)

References 10 publications

(4 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…productive area of research. Recently, we reported an annelation approach to certain eudesmane and elemane sesquiterpenes, in which the 1,6-annelation reagent 2 is used in construction of the linear tricyclic lactone 3a.1 The relative stereochemistry at C (8) and C(10) in 3 is identical with that present in dihydrocallitrisin (4), a new sesquiterpene lactone isolated from the heartwood of Callitris columellaris.2 This configuration is rare and differs from that found in the more common eudesmane sesquiterpenes such as alantolactone (5).3 Herein, we establish the flexibility of our approach to these sesquiterpenes by reporting the synthesis of (//-7,8-epialantolactone (9). In a future report, we will present the first total synthesis of (//-dihydrocallitrisin (4).…”

mentioning

confidence: 99%

Synthesis of dl-7,8-epialantolactone. A tandem SN2' dehydrobromination-organocuprate addition exemplified

et al. 1979

View full text Add to dashboard Cite

1969). (3) E. Marcus and E. Marcus, Stud. Trop. Oceanogr., 6 (l), 33-34 (1967). We collected T. crispata at Glover Reef, Belize, and were sent samples from Panama (Caribbean) by Leo Buss. (4) G. Germain, P. Main. and M. M. Woolfson. Acta Crysta//ogr., Sect. A, 27, 368-376 (1971). Synthesis of dl-7,8-Epialantolactone. A Tandem S N~' Dehydrobromination-Organocuprate Addition ExemplifiedSir:The development of methods for total synthesis of the CYmethylene-y-butyrolactones continues to be a vigorous and prqductive area of research. Recently, we reported an anne-

show abstract

mentioning

confidence: 99%

Synthesis of dl-7,8-epialantolactone. A tandem SN2' dehydrobromination-organocuprate addition exemplified

et al. 1979

View full text Add to dashboard Cite

show abstract

“…Data were also obtained suggesting that 268 is bactericidal to Escherichia coli [174]. In 1966, 4-bromomethyl-3-ethoxycarbonyl-2(5H)furanone (277 ) was synthesized in two steps starting from diethyl isopropylidenemalonate (275) (Scheme 98) [186].…”

Section: Scheme 94 Synthesis Of 3-bromo-4-(dibromomethyl)-2(5h)-furamentioning

confidence: 99%

Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents

Rossi

Lessi

Manzini

et al. 2017

COC

View full text Add to dashboard Cite

This review deals with the synthesis of unnatural and natural 2(5H)-furanone derivatives featuring bromine atoms on the heterocyclic ring and/or brominated substituents, which have been described in the literature since 1951 up to February 2016. The review has been organized on the basis of six classes of brominated furanone derivatives that were synthesized: i) 2(5H)-furanone derivatives with one bromine atom on the heterocyclic ring; ii) 2(5H)-furanone derivatives with two bromine atoms on the heterocyclic ring; iii) 2(5H)-furanone derivatives featuring one bromine atom on the heterocyclic ring and monobrominated substituents; iv) 2(5H)- furanone derivatives featuring one bromine atom on the heterocyclic ring and dibrominated substituents; v) 2(5H)-furanone derivatives with monobrominated substituents; and vi) 2(5H)-furanones featuring dibrominated substituents. Where possible, experimental details of the syntheses have been reported. Furthermore, the biological properties of the target compounds, including their mutagenic, cytotoxic, enzymatic, anti-inflammatory and photosynthetic inhibitory activities have been summarized, paying particular attention on the compounds that have demonstrated antimicrobial properties via inhibition of quorum sensing and biofilm formation

show abstract

“…[7–17] The addition of phenols and arylthiols to propiolic acids and propiolate esters gives a mixture of E and Z isomers. Recently published reaction conditions make use of alkyl amine catalysis to control E:Z ratios.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-(1-Methyl-1H-imidazol-2-ylthio)propanoic Acid and (E)-3-(1-Methyl-1H-imidazol-2-ylthio)acrylic Acid

Hattan

Shojaie

Lau

et al. 2012

Synthetic Communications

View full text Add to dashboard Cite

The syntheses of 3-(1-methyl-1H-imidazol-2-ylthio)acrylic acid and 3-(1-methyl-1H-imidazol-2-ylthio)propanoic acid, mitochondria-targeted prodrugs of the antioxidant methimazole, are described. The method of Fan et al. (Fan et al., Synthesis 2006, 2286) for the reaction of phenols with propiolic acid and propiolate esters was modified to synthesize (E)-3-(1-methyl-1H-imidazol-2-ylthio)acrylic acid. The intermediate tert-butyl (E)-3-(1-methyl-1H-imidazol-2-ylthio)acrylate was prepared by the reaction of tert-butyl propiolate with methimazole; the use of tert-butyl propiolate rather than methyl propiolate gave tert-butyl (E)-3-(1-methyl-1H-imidazol-2-ylthio)acrylate as the predominant isomer. Acid hydrolysis of the intermediate ester afforded the target compound. 3-(1-Methyl-1H-imidazol-2-ylthio)propanoic acid was synthesized from 3-bromopropanoic acid and methimazole under conditions that gave preferential substitution on sulfur and minimized substitution on nitrogen.

show abstract

Synthesen substituierter Butenolide

Abstract: Es wird die Darstellung von Butenoliden des Typs II beschrieben, und es werden die Erfahrungen diskutiert, die bei der Kondensation dieser Verbindungen mit β‐Mercapto‐acrylestern gemacht wurden.

Cited by 20 publications

References 10 publications

Synthesis of dl-7,8-epialantolactone. A tandem SN2' dehydrobromination-organocuprate addition exemplified

Synthesis of dl-7,8-epialantolactone. A tandem SN2' dehydrobromination-organocuprate addition exemplified

Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents

Synthesis of 3-(1-Methyl-1H-imidazol-2-ylthio)propanoic Acid and (E)-3-(1-Methyl-1H-imidazol-2-ylthio)acrylic Acid

Contact Info

Product

Resources

About