The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers

Kulkarni, Mukund G.; Shaikh, Yunnus B.; Borhade, Ajit S.; Dhondge, Attrimuni P.; Chavhan, Sanjay W.; Desai, Mayur P.; Birhade, Deekshaputra R.; Dhatrak, Nagorao R.; Gannimani, Ramesh

doi:10.1016/j.tetasy.2010.08.005

Cited by 24 publications

(12 citation statements)

References 40 publications

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“…MeOH, provided chromatographically separable mix of alcohols 14 a and 14 b in 1:4.05 ratio (entry 6). The stereochemical assignment of these alcohols 14 a and 14 b were established previously by our group by converting them to the known alcohols …”

Section: Resultsmentioning

confidence: 99%

An Efficient Total Synthesis of (–)‐(R), (+)‐(S)‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3,3] Claisen Rearrangement

Bhosale

Waghmode

2017

ChemistrySelect

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An efficient total synthesis of the enantiomerically pure lavandulol pheromones viz. (–)‐(R) and (+)‐(S)‐lavandulol, (–)‐(R)‐lavandulyl acetate, (–)‐(R)‐lavandulyl propionate, (+)‐(S)‐lavandulyl 2‐methylbutanoate and (+)‐(S)‐lavandulyl senecioate is accomplished from nonchiral and chiral materials. The strategy utilizes a sequence of proline catalyzed asymmetric α‐aminooxylation and [3,3] Claisen rearrangement for stereodivergent synthesis of chiral C‐2 unit containing 4‐pentenols.

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Section: Resultsmentioning

confidence: 99%

An Efficient Total Synthesis of (–)‐(R), (+)‐(S)‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3,3] Claisen Rearrangement

Bhosale

Waghmode

2017

ChemistrySelect

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“…This alcohol was oxidized using pyridiniumchlorochromate to get aldehyde-3. Aldehyde-3 was then subjected to Wittig olefination using allyloxymethylenetriphenylphosphranechloride (Kulkarni et al, 2010a;2010b) salt to get corresponding allyl-vinyl-ether-4 as an inseparable mixture of cis and trans isomers. The allyl-vinyl ether-4 so obtained was subjected to Claisen rearrangement in xylene which shows several thermolytic products.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Endangered Frog Alkaloid âEpibatidineâ, A Potent Analgesic of the Future

Dhatrak¹,

Kulkarni²

2014

Current Research in Drug Discovery

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'Epibatidine' is a nicotinic alkaloid', was first discovered in the skin of neotropical poisonous frog, 'Epipedobates tricolor' found in Ecuador. John Daly in 1974 first isolated a trace quantity of this alkaloid by scarifying several frogs. With the evolution of NMR techniques the structure of this alkaloid was reported in 1992. An year after, Nobel Laureate Prof. E.J. Corey, devised first total synthesis for this alkaloid. Since then this molecule is constantly attracting the attention of Epibatidine is an agonist at nicotinic acetylcholine receptor. Pharmacologically it is 200 to 300 times stronger than morphine and do not cause any addition. The frog species 'Epipedobates tricolor' is now been declared as endangered and therefore there is special need for easy syntheses to get the alkaloid for biological evaluations and to save these frogs from extinction. We have developed a Wittig Claisen based protocol for the total synthesis of this drug molecule which would help in investigation rest pharmacological activities of this drug. Structure of Epibatidine Molecule and the frog species from which it was isolated.

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“…Over the past two decades, isocitric acid has attracted the attention of researchers as a promising compound for the pharmaceutical and food industry [1][2][3][4][5][6][7][8][9][10][11]. The antioxidant activity of microbially produced isocitric acid exceeds that of the classic antioxidant ascorbic acid [7].…”

Section: Introductionmentioning

confidence: 99%

Isocitric Acid Production from Ethanol Industry Waste by Yarrowia lipolytica

et al. 2021

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There is ever increasing evidence that isocitric acid can be used as a promising compound with powerful antioxidant activity to combat oxidative stress. This work demonstrates the possibility of using waste product from the alcohol industry (so-called ester-aldehyde fraction) for production of isocitric acid by yeasts. The potential producer of isocitric acid from this fraction, Yarrowia lipolytica VKM Y-2373, was selected by screening of various yeast cultures. The selected strain showed sufficient growth and good acid formation in media with growth-limiting concentrations of nitrogen, sulfur, phosphorus, and magnesium. A shortage of Fe2+ and Ca2+ ions suppressed both Y. lipolytica growth and formation of isocitric acid. The preferential synthesis of isocitric acid can be regulated by changing the nature and concentration of nitrogen source, pH of cultivation medium, and concentration of ester-aldehyde fraction. Experiments in this direction allowed us to obtain 65 g/L isocitric acid with a product yield (YICA) of 0.65 g/g in four days of cultivation.

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The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers

Cited by 24 publications

References 40 publications

An Efficient Total Synthesis of (–)‐(R), (+)‐(S)‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3,3] Claisen Rearrangement

An Efficient Total Synthesis of (–)‐(R), (+)‐(S)‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3,3] Claisen Rearrangement

Total Synthesis of Endangered Frog Alkaloid âEpibatidineâ, A Potent Analgesic of the Future

Isocitric Acid Production from Ethanol Industry Waste by Yarrowia lipolytica

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The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers

Cited by 24 publications

References 40 publications

An Efficient Total Synthesis of (–)‐(R), (+)‐(S)‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3,3] Claisen Rearrangement

An Efficient Total Synthesis of (–)‐(R), (+)‐(S)‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3,3] Claisen Rearrangement

Total Synthesis of Endangered Frog Alkaloid âEpibatidineâ, A Potent Analgesic of the Future

Isocitric Acid Production from Ethanol Industry Waste by Yarrowia lipolytica

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Product

Resources

About

Total Synthesis of Endangered Frog Alkaloid âEpibatidineâ, A Potent Analgesic of the Future