A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters

Chen, Hao; Nagabandi, Srinivas; Smith, Steven G.; Goodman, Jonathan M.; Plettner, Erika

doi:10.1016/j.tetasy.2009.02.007

Cited by 8 publications

(5 citation statements)

References 43 publications

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“…The mono-and diacetates were separated by flash column chromatography and were hydrolyzed separately by NaOH in MeOH affording the corresponding enantiopure diols (+)-2 and (−)-2, as described previously. 23 The specific rotations of (+)-2 and (−)-2 {[α] D = +90.3 (c 0.6, CHCl 3 ) and [α] D = −90.7 (c 0.6, CHCl 3 )} were consistent with the literature values. 23 For the synthesis of enantiopure (+)-1a, (−)-1a, (+)-1b, and (−)-1b (Figures 3 and 4), the selective primary alcohol protection of enantiopure (+)-2 and (−)-2 with a tert- butyldimethylsilyl group was achieved in the presence of trimethyl amine and catalytic DMAP.…”

Section: ■ Results and Discussionsupporting

confidence: 87%

“…23 The specific rotations of (+)-2 and (−)-2 {[α] D = +90.3 (c 0.6, CHCl 3 ) and [α] D = −90.7 (c 0.6, CHCl 3 )} were consistent with the literature values. 23 For the synthesis of enantiopure (+)-1a, (−)-1a, (+)-1b, and (−)-1b (Figures 3 and 4), the selective primary alcohol protection of enantiopure (+)-2 and (−)-2 with a tert- butyldimethylsilyl group was achieved in the presence of trimethyl amine and catalytic DMAP. We have noticed that the less sterically hindered primary alcohol is silylated preferentially to give the major products 3 and 8.…”

Section: ■ Results and Discussionsupporting

confidence: 87%

“…The enzymatic resolution delivered the primary monoacetate for the (+)-enantiomer and the diacetate for the (−)-enantiomer (Figure ). The mono- and diacetates were separated by flash column chromatography and were hydrolyzed separately by NaOH in MeOH affording the corresponding enantiopure diols (+)- 2 and (−)- 2 , as described previously . The specific rotations of (+)- 2 and (−)- 2 {[α] D = +90.3 ( c 0.6, CHCl 3 ) and [α] D = −90.7 ( c 0.6, CHCl 3 )} were consistent with the literature values …”

Section: Resultssupporting

confidence: 68%

“…We prepared 5-(2′-hydroxyethyl)cyclopent-2-enol (±)- 2 as a precursor for the synthesis of enantiopure alicyclic ethers. , The racemic diol 2 (Figure ) was synthesized from commercially available 2,5-norbornadiene in a one-vessel and three-step reaction with 59% overall yield. The diol (±)- 2 was resolved by Lipase AK-catalyzed acetylation with neat vinyl acetate.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, Varroa destructor

Pinnelli

Singh

Soroker

et al. 2016

J. Agric. Food Chem.

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The preparation of enantiopure conformationally restricted alicyclic ethers and their inhibitory activities on the chemosensory organ of the Varroa destructor, a parasite of honey bees, are reported in this article. We tested the effect of enantiopure ethers of cis-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol on the Varroa chemosensory organ by electrophysiology, for their ability to inhibit the responses to two honey bee-produced odors that are important for the mite to locate its host: nurse bee head space odor and (E)-β-ocimene, a honey bee brood pheromone. Previous work with the racemic compounds showed that they suppress the mite's olfactory response to its bee host, which led to incorrect host choice. Based on a structure-activity relationship, we predicted that the two most active compounds-cis-1-butoxy-5-(2'-methoxyethyl)cyclopent-2-ene, cy{4,1}, and (cis-1-ethoxy-5-(2'ethoxyethyl)cyclopent-2-ene, cy{2,2}-could have opposite active enantiomers. Here we studied the enantiomers of both ethers, whose preparation involved enzymatic resolution of racemic diol cis-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol using Lipase AK with vinyl acetate. The racemic diol was prepared from commercially available 2,5-norbornadiene. We observed that the responses of the chemosensory organ to honey bee head space volatiles were significantly decreased by both enantiomers of cy{4,1} and cy{2,2}, but that responses to (E)-β-ocimene were decreased significantly only by (+)-cy{4,1} (1R,5S) and (-)-cy{2,2} (1S,5R) and not by their respective enantiomers. The importance of this result is that the racemates could be used to inhibit olfactory detection of bee odors by mites, without a loss in activity relative to the more expensive enantiopure compounds.

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Section: ■ Results and Discussionsupporting

confidence: 87%

Section: ■ Results and Discussionsupporting

confidence: 87%

Section: Resultssupporting

confidence: 68%

Section: Resultsmentioning

confidence: 99%

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Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, Varroa destructor

Pinnelli

Singh

Soroker

et al. 2016

J. Agric. Food Chem.

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“…Briefly ( Fig. 1C ), diol 1 was prepared as described in Chen et al [28] . The diol 1 was singly protected by reaction with tert-butyldimethylsilyl chloride (TBDMSCl) and imidazole in dichloromethane [10] , [27] .…”

Section: Methodsmentioning

confidence: 99%

Can We Disrupt the Sensing of Honey Bees by the Bee Parasite Varroa destructor?

et al. 2014

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BackgroundThe ectoparasitic mite, Varroa destructor, is considered to be one of the most significant threats to apiculture around the world. Chemical cues are known to play a significant role in the host-finding behavior of Varroa. The mites distinguish between bees from different task groups, and prefer nurses over foragers. We examined the possibility of disrupting the Varroa – honey bee interaction by targeting the mite's olfactory system. In particular, we examined the effect of volatile compounds, ethers of cis 5-(2′-hydroxyethyl) cyclopent-2-en-1-ol or of dihydroquinone, resorcinol or catechol. We tested the effect of these compounds on the Varroa chemosensory organ by electrophysiology and on behavior in a choice bioassay. The electrophysiological studies were conducted on the isolated foreleg. In the behavioral bioassay, the mite's preference between a nurse and a forager bee was evaluated.Principal findingsWe found that in the presence of some compounds, the response of the Varroa chemosensory organ to honey bee headspace volatiles significantly decreased. This effect was dose dependent and, for some of the compounds, long lasting (>1 min). Furthermore, disruption of the Varroa volatile detection was accompanied by a reversal of the mite's preference from a nurse to a forager bee. Long-term inhibition of the electrophysiological responses of mites to the tested compounds was a good predictor for an alteration in the mite's host preference.ConclusionsThese data indicate the potential of the selected compounds to disrupt the Varroa - honey bee associations, thus opening new avenues for Varroa control.

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Bicyclo[2.2.1]hepta-2,5-diene (Norbornadiene)

Kettles

Tam

2012

Encyclopedia of Reagents for Organic Synthesis

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A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters

Cited by 8 publications

References 43 publications

Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, Varroa destructor

Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, Varroa destructor

Can We Disrupt the Sensing of Honey Bees by the Bee Parasite Varroa destructor?

Bicyclo[2.2.1]hepta-2,5-diene (Norbornadiene)

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