Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B

Lood, Kajsa; Schmidt, Bernd

doi:10.1021/acs.joc.0c00446

Cited by 5 publications

(5 citation statements)

References 48 publications

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“…This migration has already been reported regarding citral [53]. Two problems that need to be solved for its synthesis are the formation of the acid-sensitive terminal conjugated double bonds and the trans configuration in the C 3 -C 4 double bonds [54].…”

Section: Food Science and Engineering Volume 3 Issue 2|2022| 161supporting

confidence: 52%

A Compositional Perspective of Sour Orange (Citrus aurantium L.) Flowers Essential Oil under Different Storage Conditions

Mohagheghniapour

Saharkhiz²,

Haghighi³

2022

Food Science and Engineering

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Sour orange (Citrus aurantium L.) is a tree with medicinal properties. This study assessed the impact of various storage conditions and times on the Essential Oil (EO) content of sour orange blossoms. The changes in the EO composition were recorded at the beginning of extraction and during three, six, and nine months of storage at the temperature of 4 °C (refrigerator), -20 °C (freezer), and 25 °C (room temperature) under conditions of light and darkness. According to the Gas Chromatography (GC, FID detector) and Gas Chromatography-Mass Spectrometry (GC-MS, FID detector) results, 35 compounds were identified. Linalool acetate (14.56-31.4%), linalool (18.9-23.1%), limonene (7.51-15.3%), farnesol (2.1-9%), nerolidol (6.1-8.9%), β-pinene (5.7-8.7%), trans-β-ocimene (0-7.9%), and geranyl acetate (4.2-5.7%) constituted the major EO components in different storage treatments. After nine months, linalool acetate climbed by more than twice as much. Overall, the principal EO compositions are significantly impacted by the storage circumstances. Such knowledge is essential for the food and pharmaceutical industries to use EO effectively in their intended products.

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Section: Food Science and Engineering Volume 3 Issue 2|2022| 161supporting

confidence: 52%

A Compositional Perspective of Sour Orange (Citrus aurantium L.) Flowers Essential Oil under Different Storage Conditions

Mohagheghniapour

Saharkhiz²,

Haghighi³

2022

Food Science and Engineering

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“…Unfortunately, synthesis of hydroxydiene units is rather rare. Preliminary tentative synthesis of the conjugated hydroxydiene inspired by the work of Schmidt and coworkers was not successful [ 9 ].…”

Section: Resultsmentioning

confidence: 99%

“…(R)-4-((Hept-6-yn-1-yloxy)methyl)-2,2-dimethyl-1,3-dioxolane ( 4 ): Prepared following the literature procedure described in the literature [ 9 ]: ( R )-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (4.3 g, 32.5 mmol) was dissolved in dimethylformamide (100 mL) at 0 °C under an inert atmosphere. Sodium hydride (60% wt, 1.56 g, 35 mmol) was added in several portions.…”

Section: Methodsmentioning

confidence: 99%

Isolation, Synthesis and Absolute Configuration of the Pericharaxins A and B, Epimeric Hydroxy-Polyene Glycerol Ethers from the Calcarean Sponge Pericharax heteroraphis

et al. 2022

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Naturally occurring epimeric hydroxy-polyene glycerol ether pericharaxins A (1a) and B (1b) were isolated from the calcarean sponge Pericharax heteroraphis. The structural and stereochemical characterization of both diastereoisomers were established on the basis of spectroscopic data analysis and total synthesis in seven steps. The mixture of pericharaxins A (1a) and B (1b) was proven to be epimeric by chiral-phase HPLC analysis of both synthetic and natural samples. Further separation of the epimers and application of Mosher’s method to the synthetic compounds allowed unequivocal absolute configuration assignment. While natural products and the synthetic intermediates were shown to be non-cytotoxic on the HCT116 cell line, the endochondral differentiation activity using human type X collagen transcription activity in ATDC5 cells is interesting.

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“…The total synthesis of the (+)‐Bretonin B 129 , amarine natural product, which possesses conjugated polyenes was reported by Schmidt et al (Scheme 23). [44] They demonstrated that combining a Julia‐Kocienski reaction with tethered RCM reaction result in an adaptable and efficient synthesis of E, Z, E‐ trienes, as evidenced by Bretonin B. The synthesis of (+)‐Bretonin B involves the reaction of sulfone 126 with aldehyde 127 which led to the formation of the product 128 through Julia‐Kocienski olefination.…”

Section: Applications Of Julia‐kocienski Olefination In Natural Produ...mentioning

confidence: 99%

Recent Applications and Trends in the Julia‐Kocienski Olefination

Rinu¹,

Radhika²,

Anilkumar³

2022

ChemistrySelect

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The Julia-Kocienski (J-K) olefination is a modified version of Julia-Lythgoe olefination. In this reaction, an aldehyde or ketone is coupled with heterocycle-bearing sulfone in the presence of a strong base to yield alkene. It has shown wide application in the synthesis of olefinic fragments in natural product synthesis. The Julia-Kocienski olefination is one of the most efficient protocols for the synthesis of E-alkenes. Nowa-days, a variety of natural products were synthesised by using the Julia-Kocienski olefination as the key step, and several developments and modifications were witnessed in this area. This review comprehends the recent developments and achievements in Julia-Kocienski olefination along with its application in natural product synthesis covering literature from 2016 to 2021.

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Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B

Cited by 5 publications

References 48 publications

A Compositional Perspective of Sour Orange (Citrus aurantium L.) Flowers Essential Oil under Different Storage Conditions

A Compositional Perspective of Sour Orange (Citrus aurantium L.) Flowers Essential Oil under Different Storage Conditions

Isolation, Synthesis and Absolute Configuration of the Pericharaxins A and B, Epimeric Hydroxy-Polyene Glycerol Ethers from the Calcarean Sponge Pericharax heteroraphis

Recent Applications and Trends in the Julia‐Kocienski Olefination

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