Method for alkylating lactones

Herrmann, J.; Schlessinger, R. H.

doi:10.1039/c39730000711

Cited by 60 publications

(75 citation statements)

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“…18) Butyrolactone 3 was then reacted with 5-iodo-2-methyl-2-pentene dissolved in hexamethylphosphoramide (HMPA) by using lithium diisopropylamide (LDA) to give a-(4-methyl-3-pentenyl)-a-methylthio-g-butyrolactone (4, 57z) as reported. 19) Oxidation of 4 by 2KHSO 5 ・ KHSO4K2SO4 (OXONE) as reported 20) gave a-(4-methyl-3-pentenyl)-a-methylsulfonyl-g-butyrolactone (5, 50z). Butyrolactone 5 was re‰uxed in toluene to give target compound 1 (87z).…”

Section: -(4-methylmentioning

confidence: 94%

3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide:

Tarui¹,

Mori²,

Nishida³

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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A new monoterpene lactone from the acarid mite, Schwiebea araujoae, was elucidated without its isolation by GC/FT-IR and GC/MS analyses to be 3-(4-methyl-3-pentenyl)-2(5H)-furanone (1) and tentatively named as alpha,alpha-acariolide. The structure of 1 was identified by its synthesis from alpha-bromo-gamma-butyrolactone via 4 reaction steps. The synthesized compound gave the same GC/MS and GC/FT-IR spectra as those of the natural product. The other monoterpene lactone was likewise elucidated from the unidentified Rhizoglyphus mite to be 4-(4-methyl-3-pentenyl)-2(5H)-furanone (2) and named as alpha,beta-acariolide; it was also identified by its synthesis in 5 reaction steps from the same butyrolactone as the starting material. GC/MS and GC/FT-IR spectra of the preparation were identical to those of the natural product.

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Section: -(4-methylmentioning

confidence: 94%

3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide:

Tarui¹,

Mori²,

Nishida³

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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“…Tris(dibenzylideneacetone)dipalladium (0) (Pd 2 (dba) 3 ), palladium (II) acetate (Pd(OAc) 2 ), tetrakis(acetonitrile)palladium(II) tetrafluoroborate ((MeCN) 4 Pd(BF 4 ) 2 ), 9,9-dimethyl-4,5-bis (diphenylphosphino)xanthene (XANTPhos), alpha, alpha'-bis(di-tert-butylphosphino)-ortho-xylene (97+%) (DtBPX), tricyclohexylphosphine (97+%) (PCy 3 ), and 1,4-bis(diphenylphosphino)butane (dppb) were purchased from Strem and used as received. 2-Methylvalerolactone [53][54][55] and 2-ethylbutyrolactone [56] were synthesized according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Catalytic carbonylation of 4-penten-1-ol to ɛ-caprolactone and oligocaprolactone

Funk

Newsham

Goldstein

et al. 2005

Journal of Molecular Catalysis A: Chemical

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“…An early example of this was the synthesis of a-methyl-dVL in which the excipient enolate was quenched with methyl iodide at À40 C. 92 Homopolymerization of this monomer has only been achieved in the bulk under argon with a lipase catalyst derived from Candida antarctica at 35 C obtaining a M n of 8500 g mol À1 and PDI of 2.1. 93 More recently a-allyl-dVL, 30, was synthesized in an analogous manner from dVL and allyl bromide.…”

Section: D-and B-lactonesmentioning

confidence: 99%

Towards poly(ester) nanoparticles: recent advances in the synthesis of functional poly(ester)s by ring-opening polymerization

2010

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The recent trends in the synthesis of functional poly(ester)s by ring-opening polymerization (ROP) are reviewed. While the use of ROP processes for the synthesis of poly(lactide), poly(lactide-co-glycolide) and several poly(lactone)s has been well studied, the paucity of functional groups available for further reaction limits their application. Recent efforts to expand this available functionality are reviewed focusing on the application of renewable resources in the synthesis of new monomers and the utilization of click chemistry to provide common intermediate polymers in the manipulation of poly(ester) functionality. In turn these advances are leading to a new generation of precisely controlled nanoparticles comprised entirely of poly(ester)s.

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Method for alkylating lactones

Cited by 60 publications

References 0 publications

3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide:

3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide:

Catalytic carbonylation of 4-penten-1-ol to ɛ-caprolactone and oligocaprolactone

Towards poly(ester) nanoparticles: recent advances in the synthesis of functional poly(ester)s by ring-opening polymerization

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