The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol

Curran, Timothy T.; Hay, David; Koegel, C. P.; Evans, Jonathan

doi:10.1016/s0040-4020(96)01169-6

Cited by 80 publications

(78 citation statements)

References 60 publications

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“…Those with small and few substituents, such as cyclopent-4-ene-1,3-diyl diacetate (80% yield, 20.5% ee) [34], cyclohex-2-en-1-yl acetate [35], 4-hydroxycyclopent-2-en-1-one (E = 11) [36], 4-hydroxy-2-methyl-2-cyclopentenone (60% yield, 60% ee) [37], 3-bromocyclopent-2-enol [38] give less enantiopure products. An exception is the meso compounds [43][44][45][46][47][48][49], however here the stereo differentiation is based on a different principle.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

Chen

Hanefeld

2013

Journal of Molecular Catalysis B: Enzymatic

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Section: Resultsmentioning

confidence: 99%

Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

Chen

Hanefeld

2013

Journal of Molecular Catalysis B: Enzymatic

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“…As far as we can tell, this is the first time an enzymatic kinetic resolution using Lipase AK has been employed to separate a racemic mixture of the mono-PMB ether of cyclopent-1-ene-3,5-diol derivatives, although several other ethers have been used. 17 The conversion of the enantiomerically enriched cyclopentenol 11 to the desired S 2-bromo-4-arylmethoxycyclopentenone 14 was achieved in two steps, via oxidation to the enone 13 with pyridinium chlorochromate (PCC, 89%) followed by bromination in the presence of triethylamine to give 14 in 80% yield. The enantiomeric R 2-bromo-4-aryl- methoxycyclopentenone 16 was prepared in three steps from 12 via deprotection of the acetate and PCC oxidation to give the enone 15 in 87% yield followed by bromination in the presence of base to give 16 in 80% yield.…”

Section: Resultsmentioning

confidence: 99%

An Epoxyisoprostane Is a Major Regulator of Endothelial Cell Function

Zhong¹,

Springstead²,

Al-Mubarak

et al. 2013

J. Med. Chem.

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The goal of these studies was to determine the effect of 5,6-epoxyisoprostane, EI, on human aortic endothelial cells (HAEC). EI can form as a phospholipase product of 1-palmitoyl-2-(5,6-epoxyisoprostane E2)-sn-glycero-3-phosphocholine, PEIPC, a pro-inflammatory molecule that accumulates in sites of inflammation where phospholipases are also increased. To determine the effect of EI on HAEC, we synthesized several stereoisomers of EI using a convergent approach from the individual optically pure building blocks, the epoxyaldehydes 5 and 6 and the bromoenones 14 and 16. The desired stereoisomer of EI can be prepared from these materials in only six operations and thus large amounts of the product can be obtained. The trans/trans isomers had the most potent activity, suggesting specificity in the interaction of EI with the cell surface. EI has potent anti-inflammatory effects in HAEC. EI strongly inhibits the production of MCP-1, a major monocyte chemotactic factor, and either decreases or minimally increases the levels of ten pro-inflammatory molecules increased by PEIPC. EI also strongly downregulates the inflammatory effects of IL-1β, a major inflammatory cytokine. Thus EI, a hydrolytic product of PEIPC, has potent anti-inflammatory function.

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“…The syntheses of γ‐substituted cyclopentenones of type B commenced with the known enone 4‐hydroxy‐2‐cyclopenten‐1‐one ( rac ‐ 2 )12 (Scheme…”

Section: Resultsmentioning

confidence: 99%

Intramolecular [2+2] Photocycloaddition Reactions as an Entry to the 2‐Oxatricyclo[4.2.1.0^4, 9]nonan‐3‐one Skeleton of Lactiflorin

Lü

Herdtweck

Bach

2012

Chemistry An Asian Journal

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Two [2+2] photocycloaddition routes were evaluated as possible ways to access the tricyclic core structure found in the terpene monoglycoside lactiflorin. While the first route via γ-substituted cyclopentenones was quickly discarded, the reactions of racemic (5R*)-3-benzyloxy-5-but-3'-enyl-4-methoxycarbonylfuran-2(5H)-ones proceeded in high yields and with perfect diastereoselectivity. However, it turned out that the regioselectivity was strongly dependent on the substitution pattern within the but-3'-enyl chain, which connects the terminal olefinic double bond to the photoexcited butenolide chromophor. If the chain was unsubstituted or if a tert-butyldimethylsilyloxy group was placed at the 2' position in a syn-relationship to the existing stereogenic center (5R*,2'S*), the crossed product prevailed with regioselectivities of 89:11 to 69:31. If the tert-butyldimethylsilyloxy group was positioned at 2' in an anti-relationship to the existing stereogenic center (5R*,2'R*), the desired straight products were obtained in regioselectivities of 74:24 to 55:45 (61-83% yield). Following this route, the aglycon part of lactiflorin was obtained by an intramolecular [2+2] photocycloaddition and a subsequent hydrogenolysis in 53% yield. Its further conversion into the natural product after glycosylation included a methyl addition to the lactone carbonyl group, which was optimized to give the desired key intermediate in a yield of 70%. The further conversion to lactiflorin was achieved in four steps and with an overall yield of 49%.

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The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol

Cited by 80 publications

References 60 publications

Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

An Epoxyisoprostane Is a Major Regulator of Endothelial Cell Function

Intramolecular [2+2] Photocycloaddition Reactions as an Entry to the 2‐Oxatricyclo[4.2.1.0^4, 9]nonan‐3‐one Skeleton of Lactiflorin

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The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol

Cited by 80 publications

References 60 publications

Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

An Epoxyisoprostane Is a Major Regulator of Endothelial Cell Function

Intramolecular [2+2] Photocycloaddition Reactions as an Entry to the 2‐Oxatricyclo[4.2.1.04, 9]nonan‐3‐one Skeleton of Lactiflorin

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Intramolecular [2+2] Photocycloaddition Reactions as an Entry to the 2‐Oxatricyclo[4.2.1.0^4, 9]nonan‐3‐one Skeleton of Lactiflorin