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Journal ArticleDOI

Novel molecular rearrangements of 4 hydroxy 2 cyclopentenones

01 Jan 1985-Tetrahedron (Elsevier Limited)-Vol. 41, Iss: 2, pp 435-450
TL;DR: In this article, the stereochemistry of the rearrangement is interpreted as the result of synchronous enolate induced [1.5]-sigmatropic rearrangements and stepwise addition-elimination process.
About: This article is published in Tetrahedron.The article was published on 1985-01-01. It has received 9 citations till now. The article focuses on the topics: Sigmatropic reaction & Enone.
Citations
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177 citations

Journal ArticleDOI
TL;DR: A highly efficient one-pot transformation of readily accessible furans into 4-hydroxy-2-cyclopentenones in H2O, using singlet oxygen as oxidant, has been developed.
Abstract: A highly efficient one-pot transformation of readily accessible furans into 4-hydroxy-2-cyclopentenones in H2O, using singlet oxygen as oxidant, has been developed.

49 citations

Journal ArticleDOI
TL;DR: In this paper, a process for the synthesis of kilogram quantities of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for prostaglandin analogue drugs, was described.

19 citations

Journal ArticleDOI
TL;DR: In this article, a method for the preparation of (S)-4-hydroxy-2-methylcyclopent-2en-1-one from 1-(2-furyl)ethanol using modified Piancatelli rearrangement and enzymatic kinetic resolution of the racemate was developed.

13 citations

Journal ArticleDOI
TL;DR: In this article, the authors compared the efficiency of 20 novel routes for the synthesis of methyl jasmonate via the strategic intermediates 3, 4, and 6a, and constructed a synthetic network via the diverse intermediates 7, 10, 13, 14, 17, and 18.
Abstract: For the synthesis of methyl jasmonate (1), via the strategic intermediates 3, 4, and 6a, we constructed a synthetic network via the diverse intermediates 7–10, 13, 14, 17, and 18. This allowed us to compare the efficiency of more than 20 novel routes. The most productive pathway with a total yield of 38% is represented by the sequence→5a→5m→13b→13a→6a→4 and proceeds via sequential bromination, basic elimination, decarbomethoxylation, isomerization, and finally Lindlar hydrogenation. The shortest selective way, 2a→[(E,E)-12b]→3→4, is a two-pot sequence using a modification of Naef's method, based on an aldol condensation between inexpensive cyclopentanone (2a) and crotonaldehyde, with in situ CoreyChaykovsky cyclopropanation under phase transfer conditions. The key intermediate 3 was then simply pyrolyzed to afford 4 in 27% total yield. The alternative isomerization method via the six-step deviation→5a→5c→8c→13a→6a→4 was longer, although more efficient, with a total yield of 32%. Alternatively, a yield of 34% was obtained via the five-step sequence→5a→5c→2h→2i→4. Another favored six-step pathway,→5a→5c→2h→17a→14a→4 afforded the target compound in 35% total yield.

6 citations

References
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TL;DR: The application of thiazolium salt catalysed addition of aldehydes to α,β-unsaturated esters for the synthesis of the title compounds (1, 2 and 3) is discussed in this paper.
Abstract: The application of thiazolium salt catalysed addition of aldehydes to α,β-unsaturated esters for the synthesis of the title compounds (1, 2 and 3) is discussed. Anwendung von Carbonyl Umpolung fur Prostaglandin Synthese, III1). Synthese von Synthonen der 11-Desoxy-prostaglandine2) Der Einsatz der Thiazoliumsalz-katalysierten Addition von Aldehyden an α,β-ungesattigte Ester fur die Synthese der Titelverbindungen (1, 2 und 3) wird diskutiert.

29 citations