The Facile Synthesis of Lactones

Mukaiyama, Teruaki; Usui, Masahiro; Saigo, Kazuhiko

doi:10.1246/cl.1976.49

Cited by 246 publications

(176 citation statements)

References 10 publications

Supporting

Mentioning

169

Contrasting

Unclassified

Order By: Relevance

“…20 The conversion of the macrolactone 2 into the analogues 9 and 10 commenced with benzylic bromination, according to classical conditions (NBSbenzoyl peroxide). After several attempts, we found that the bromine lactone 6 was quantitatively converted into trans-unsaturated lactone 7 by treatment with DBU in refluxing benzene under a nitrogen atmosphere.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of new salicylate macrolactones from anacardic acids

Logrado¹,

Silveira

Romeiro

et al. 2005

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

No âmbito de uma linha de pesquisa que visa a obtenção de novas substâncias bioativas, a partir de lipídeos fenólicos não-isoprenóides de Anacardium occidentale, descrevemos a síntese e avaliação citotóxica de novas macrolactonas salicílicas, preparadas a partir da mistura de ácidos anacárdicos, principal constituinte do líquido da casca da castanha de caju (LCC) in natura.In connection with our ongoing investigation in the search for new bioactive compounds using non-isoprenoid phenolic lipids from Anacardium occidentale as starting material, we describe the synthesis and cytotoxicity screening of some novel salicylate macrolactones prepared from anacardic acids, the major constitutents of natural cashew nut-shell liquid (CNSL). Keywords: cashew nut shell liquid, anacardic acids, salicylate macrolactones IntroductionNon-isoprenoid phenolic lipids exist in plants from a number of different families, notably the Anacardiaceae shrub, many small plants, and certain bacterial sources. The cashew tree (Anacardium occidentale), a species originally native to Brazil where it is still cultivated, also grown in a large number of other tropical and sub-tropical countries, represents one of the major and cheapest sources of this class of compounds. 1 As the main component of natural cashew nut-shell liquid (CNSL), anacardic acids (1) are the most widely distributed phenolic lipids. Chemically, the anacardic acids feature a convenient salicylic acid system and a long sidechain at the 6-position, in which a double bond is found at C-8 in the monoene, diene and triene components ( Figure 1). Anacardic acids are reported to exhibit a variety of biological activities, 2 and also have stimulated much research in order to prepare drug analogues for application in several fields. 3 In the course of ongoing investigations aiming at new drug candidates, the particular structural behavior and abundance of anacardic acids have prompted us to search for a strategy to convert these materials into analogues of an emerging family of antitumor natural products, for example: oximidines I, II, and III, 4 apicularens A and B, 5 and salicylhalamides A and B 6 (Figure 2), which present a benzofused macrolactone bearing an unusual N-acylated enamide 1218 Logrado et al. J. Braz. Chem. Soc. side-chain. Related to the fact that these benzolactone enamides do not display any significant structural correlations to the profiles of known anti-cancer drugs, they constitute a very attractive new class of lead compounds in the search for antineoplastic agents and have therefore shown considerable interest concerning to isolation, chemical synthesis and mechanistic studies of the biochemical mode of action. [4][5][6][7] Other macrolactones structurally related to the above macrolides include lasiodiplodin, 8 cis-and transresorcylide, 9 and curvularin 10 ( Figure 3). These orsellinic acid type macrolides also have attracted the attention of many synthetic chemists regarding both chemical and physiological activities. 11-13 For instance, methyldehydrola...

show abstract

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of new salicylate macrolactones from anacardic acids

Logrado¹,

Silveira

Romeiro

et al. 2005

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…The crown ethers have been characterized by 1 H NMR, 13 C NMR, GC-MS, and/or HRMS (highresolution mass spectrometry) techniques, FTIR, and CD-spectroscopy (the latter two characterization techScheme 1 (a) NaNO2, H2SO4, H2O, RT (54%); (b) EtOH, HCl, PhMe, ∆ (75%); (c) DHP, TsOH, Et2O, RT (87%, 95%); (d) LiAlH4, Et2O, RT (94%, 92%); (e) (1) TsO(CH2CH2O)2Bn (37), KOH, THF, ∆ and (2) TsOH, MeOH, RT (68%, 73%); (f) BrCH2COOtert-Bu, tertBuOK, tert-BuOH, RT (72%, 78%); (g) TFA, RT (97%, 93%); (h) Pd/C, H2, dioxane, RT (100%, 100%); (i) CoCl2, 250°C, p ≈ 5 mmHg (72%, 56%). The yields in parentheses refer to the isobutyl-and methyl-substituted compounds, respectively.…”

Section: )mentioning

confidence: 99%

“…The 1 H NMR and 13 C NMR spectra of the polymers 1-3 suggest that polymerization is not accompanied by significant degradation or side reactions. As an example the 13 C NMR spectrum of polymer 1 is shown in Figure 4: the spectrum accounts for no more than the expected 22 carbons. Molecular weights of the polymers could not be determined by 1 H NMR, since the end group protons could not be detected separately.…”

Section: Acids (S)-32 (S)-21 and (S)-22mentioning

confidence: 99%

“…13 C-NMR spectra were taken on the Bruker spectrometer at 101 MHz with the solvent as standard. In some cases, inverse-gated decoupled 13 C NMR was conducted to be able to integrate the carbon peaks. UV/vis measurements were performed on a PE UV/Vis Spectrophotometer Lambda 2B.…”

Section: General Compounds (S)-8 (S)-9 (S)-11 (S)-12 (S)-13 (S)-mentioning

confidence: 99%

“…The collected organic , OCH′H′′COOH), 3.75-3.45 (11H, m), 1.8 (1H, m, CH2CH(CH3)2), 1.4 (1H, ddd, 2 J ) 13.9 Hz, 3 J ) 7.3 Hz, 3 J ) 6.2 Hz, CHCH′H′′CH(CH3)2), 1.25 (1H, ddd, 2 J ) 13.9 Hz, 3 J ) 7.7 Hz, 3 J ) 5.9 Hz, CHCH′H′′CH(CH3)2), 0.95 (6H, dd, 3 J ) 6.7 Hz, 3 J ) 6.7 Hz, CH2CH(CH3)2). 13 , ((S)-20). Compound (S)-18 (6.5 g, 17.7 mmol) was coevaporated twice with CHCl3 before TFA (20.1 g, 176 mmol) was added dropwise.…”

Section: S)-1-[2-(2-(benzyloxy)ethoxy)ethoxy]propan-2-ol ((S)-16)mentioning

confidence: 99%

See 2 more Smart Citations

Unconventional, Amphiphilic Polymers Based on Chiral Poly(ethylene oxide) Derivatives. I. Synthesis and Characterization

et al. 1997

View full text Add to dashboard Cite

The first representatives of a new class of synthetic, amphiphilic polymersspolyethylene oxide-based (PEO-based) polymers 1-3, (see Figure 2)sare introduced. These polymers are constituted in a similar way as coiled-coil-forming peptides: the polymers possess a regular repeat of apolar (A) residues in a polar (P) sequence of residues. Polymers 1-3 can thus be characterized by the formula [PAPPAPP′]n or [PAPP′]n, in which P stands for an ethylene oxide unit, P′ stands for a glycate unit, and A stands for a hydrophobically modified ethylene oxide unit. The preparation of 1-3 comprises the synthesis and SnOct2-catalyzed ring-opening polymerization of 2-oxo-crown ether monomers (SS)-4, (S)-5, and (S)-6. Alternatively, polymers 1-3 have been obtained by the polycondensation of their ω-hydroxycarboxylic acid precursors. 1 H NMR and 13 C NMR analysis as well as electrospray mass spectrometry (ES-MS) verified the integrity of the followed synthetic route and, therefore, confirmed the regular repeat of polar and apolar segments in 1-3. The critical aggregation concentrations (cac's) of 1-3 in H2O at 20°C were determined by a fluorescence study, using pyrene as an apolar fluorescent probe. The cac's (i) were strongly influenced by the size of the hydrophobic segments in the polymer and by the frequency at which these segments were repeated in the polymer and (ii) varied over a wide concentration range (i.e. polymer 1 displayed a cac of ca. 0.002 mg/mL, whereas polymer 3 showed a cac of ca. 0.15 mg/mL). Thus, tailoring of the cac is possible in these new synthetic, amphiphilic polymers.

show abstract

Structure-Reactivity Relationship in the Reaction of Highly Reactive Zinc with Alkyl Bromides

Guijarro¹,

Rieke²

1998

Angewandte Chemie International Edition

View full text Add to dashboard Cite

show abstract

The Facile Synthesis of Lactones

Cited by 246 publications

References 10 publications

Synthesis and biological evaluation of new salicylate macrolactones from anacardic acids

Synthesis and biological evaluation of new salicylate macrolactones from anacardic acids

Unconventional, Amphiphilic Polymers Based on Chiral Poly(ethylene oxide) Derivatives. I. Synthesis and Characterization

Structure-Reactivity Relationship in the Reaction of Highly Reactive Zinc with Alkyl Bromides

Contact Info

Product

Resources

About