Novel convenient synthesis of (Z/E)-8-dodecenyl acetates, components of the Grapholitha molesta sex pheromone

Huang, Guozheng; Li, J. M.; Lü, Jian; Aisa, Haji Akber

doi:10.1007/s10600-006-0263-7

Cited by 7 publications

(4 citation statements)

References 11 publications

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“…Applied substrates gave very high yields of target products in all cases; however, a longer reaction time was required for 3-methyl-2-buten-1-ol (Table , entry 8). 3-Methylbut-2-enyl acetate ( 3i ) is a starting material for the synthesis of tryprostatins A and B, mammalian cell cycle inhibitors, while 9-decen-1-yl acetate ( 3j ) and (2 Z )-pent-2-en-1-yl acetate ( 3l ) are building blocks for plant regulators and sex pheromones . The component of the antiproliferative agent against human solid tumor cell lines HBL-100 (breast), HeLa (cervix), SW1573 (nonsmall cell lung), T-47D (breast), and WiDr (colon).…”

Section: Resultsmentioning

confidence: 99%

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

et al. 2021

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Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.

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Section: Resultsmentioning

confidence: 99%

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

et al. 2021

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“…8-Oxooctyl acetate ( 2a ) was obtained as a colorless liquid (125 mg, 81%). The spectroscopic data of 8-oxooctyl acetate ( 2a ) matched those reported in the literature …”

Section: Methodsmentioning

confidence: 99%

“…The spectroscopic data of 8-oxooctyl acetate (2a) matched those reported in the literature. 34 1 H NMR (500 MHz, CDCl 3 ): δ H 9.77 (s, 1H), 4.05 (t, J = 6.7 Hz, 2H), 2.43 (tt, J = 7.3, 1.6 Hz, 2H), 2.04 (d, J = 1.4 Hz, 3H), 1.63 (q, J = 6.8 Hz, 4H), 1.43−1.23 (m, 6H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ): δ C 202.7, 171.3, 64.5, 43.9, 29.1, 29.0, 28.6, 25.8, 22.0, 21.0.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Surfactant-Assisted Ozonolysis of Alkenes in Water: Mitigation of Frothing Using Coolade as a Low-Foaming Surfactant

et al. 2022

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Aqueous-phase ozonolysis in the atmosphere is an important process during cloud and fog formation. Water in the atmosphere acts as both a reaction medium and a reductant during the ozonolysis. Inspired by the atmospheric aqueous-phase ozonolysis, we herein report the ozonolysis of alkenes in water assisted by surfactants. Several types of surfactants, including anionic, cationic, and nonionic surfactants, were investigated. Although most surfactants enhanced the solubility of alkenes in water, they also generated excessive foaming during the ozone bubbling, which led to the loss of products. Mitigation of the frothing was accomplished by using Coolade as a nonionic and low-foaming surfactant. Coolade-assisted ozonolysis of alkenes in water provided the desired carbonyl products in good yields and comparable to those achieved in organic solvents. During the ozonolysis reaction, water molecules trapped within the polyethylene glycol region of Coolade were proposed to intercept the Criegee intermediate to provide a hydroxy hydroperoxide intermediate. Decomposition of the hydroxy hydroperoxide led to formation of the carbonyl product without the need for a reductant typically required for the conventional ozonolysis using organic solvents. This study presents Coolade as an effective surfactant to improve the solubility of alkenes while mitigating frothing during the ozonolysis in water.

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“…It was observed that an impurity (up to 10%) of the (E)-isomer (299b) did not inhibit its activity. A short synthetic scheme [91] for a mixture (72.5:27.5) of acetates 299a and b started from 10-hydroxydecanoic acid (294) and used ozonolysis of 9-nonenylacetate (297) to prepare aldehyde 298 and Wittig olefination of the last. In turn, the carbon chain of starting hydroxyacid 294 was shortened by dehydrobromination of 296, which was obtained by Hunsdiecker decarboxylation from acetoxyacid 295 (Scheme 42).…”

Section: -Undecenoic Acidmentioning

confidence: 99%

Ozonolysis of Unsaturated Compounds in the Synthesis of Insect Pheromones and Juvenoids

et al. 2015

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Novel convenient synthesis of (Z/E)-8-dodecenyl acetates, components of the Grapholitha molesta sex pheromone

Cited by 7 publications

References 11 publications

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

Surfactant-Assisted Ozonolysis of Alkenes in Water: Mitigation of Frothing Using Coolade as a Low-Foaming Surfactant

Ozonolysis of Unsaturated Compounds in the Synthesis of Insect Pheromones and Juvenoids

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