Simple One-Pot Synthesis of Macrocyclic Dichalcones by Twofold Aldol Condensation, and the Effect of Cesium Ion

Vögtle, Fritz; Mayenfels, P.; Luppertz, Friedhelm

doi:10.1055/s-1984-30898

Cited by 11 publications

(4 citation statements)

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“…Our diols melted at 117.5" and 134.5", respectively, and a comparison of the reported 'H-NMR data with the present values clearly shows that the earlier workers also must have had obtained a mixture 35 and 3S', whichin additionwas contaminated with some undefined impurities. For a successful application of CsOH to bring about aldol condensations, see [48]. With the required reference compound (Jt)-4 at hand, the neutral fractions of the mycelium extracts of S. araneosa CAIN were investigated once more.…”

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confidence: 99%

Synthesis of the Dolabellane Diterpene Hydrocarbon (±)‐δ‐araneosene

Jenny¹,

Borschberg²

1995

Helvetica Chimica Acta

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The racemic form of the bicyclic diterpene hydrocarbon 6 -araneosene (4), endowed with the dolahellane skeleton, was prepared from geraniol in two different ways. The more efficient route involved 13 steps and proceeded with an overall yield of 3.6% (average: 77% per step). With this reference sample at hand, the hitherto elusive metabolite (-)-4, a likely biogenetic precursor of cycloaraneosene ((-)-3) and sordaricin ((-)-1), could finally be isolated in 2 99.5% purity from the neutral fractions of the mold Sorduriu uraneosu CAIN (Ascomycetes).

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confidence: 99%

Synthesis of the Dolabellane Diterpene Hydrocarbon (±)‐δ‐araneosene

Jenny¹,

Borschberg²

1995

Helvetica Chimica Acta

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“…The yields of the compounds 3 which are of major interest here, have been found to be much better than those for some related compounds reported by other groups. 18,19 This category of compounds has the potential to find wide applicability as two of their spacers can be varied independently and widely and the two α,β-unsaturated ketone moieties present in each of them can be made to undergo condensation with varieties of suitable heteroatom containing condensing agents leading to interesting heterocycle fused macrocycles. Some works in this direction are being done currently.…”

Section: Discussionmentioning

confidence: 99%

“…The chemical literature shows sporadic reports of construction of a few such types of compounds. [18][19][20] Synthesis of other structurally related compounds and their suitable transformations to useful hosts are also reported. 21,22 Furthermore, very recently several types of macrocycles containing fused heterocyclic or homocyclic moieties have been synthesized [23][24][25][26][27][28][29] and a good number of them have shown some very interesting properties.…”

Section: Introductionmentioning

confidence: 99%

Simple synthesis of a new family of 22- to 28-membered macrocycles containing two chalcone moieties

Mondal¹,

Mandal²,

Mallik³

2012

Arkivoc

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A new family of 22-to 28-membered tetrabenzo-macrocycles containing two chalcone moieties has been synthesized from 2-hydroxybenzaldehyde and 2′-hydroxyacetophenone through phenol alkylation with α,ω-dibromoalkanes followed by Claisen-Schmidt reaction under high dilution condition. All the compounds of this family were found to possess both the double bonds in Econfiguration. An attempt to synthesize another family of isomeric tetrabenzo-macrocycles having opposite alignment of the two chalcone moieties by reaction of 2,2′-dihydroxychalcone with α,ω-dibromoalkanes was not successful, a series of 12-to 14-membered dibenzomacrocycles with only one chalcone moiety was obtained here.

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“…This paper describes the first successful synthesis of a 1,9-dithia[2.2]paracyclophane ( 1 ), its properties, and its molecular structure as determined by X-ray crystallography. The synthesis is accomplished by the application of both a cesium effect , and a high dilution effect …”

Section: Introductionmentioning

confidence: 99%