1986
DOI: 10.1055/s-1986-31615
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Advances in the Synthesis of α-Methylenelactones

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Cited by 148 publications
(25 citation statements)
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“…5-Hydroxyhexanoate 16a was completely converted into the lactone 17a by treatment of the obtained mixture with CF 3 CO 2 H in DCM. 31 P NMR data of the lactone 17a revealed the formation of two diastereoisomers in a ratio 0.67:1. In order to find an effective, alternative procedure for the highly diastereoselective synthesis of the lactone 17a we examined the stereoselectivity of the reduction of the oxoester 15a in the presence of selected metal salts.…”
Section: Chemistrymentioning
confidence: 99%
See 1 more Smart Citation
“…5-Hydroxyhexanoate 16a was completely converted into the lactone 17a by treatment of the obtained mixture with CF 3 CO 2 H in DCM. 31 P NMR data of the lactone 17a revealed the formation of two diastereoisomers in a ratio 0.67:1. In order to find an effective, alternative procedure for the highly diastereoselective synthesis of the lactone 17a we examined the stereoselectivity of the reduction of the oxoester 15a in the presence of selected metal salts.…”
Section: Chemistrymentioning
confidence: 99%
“…1. Many methods of their preparation have been reported in the literature [24][25][26][27][28][29][30][31][32][33][34][35][36]. a-Methylene-d-lactones 2 also can act as Michael acceptors, therefore it is really surprising that the data about the cytotoxic activity of these compounds are scarce and no systematic SAR investigations have been undertaken so far.…”
Section: Introductionmentioning
confidence: 99%
“…1 In this context, paraconic acids (bearing a carboxylic acid function at the position b to the carbonyl, see Scheme 1), constitute an important class of c-butyrolactones that showed antitumor and antibiotic activies. 2 Due to the important biological activities of paraconic acids, several methods have been described for the synthesis of natural products containing b-carboxylated c-butyrolactones, including a variation of the Perkin-Fittig condensation, 3 multicomponent reactions, 4 ring-closing metathesis of two electron deficient olefins, 5 free-radical-mediated conjugate additions, 6 and aldol reactions of dioxanes.…”
Section: Introductionmentioning
confidence: 99%
“…For a living radical system, all chains are initiated at the same time and grow at approximately the same rate, as a consequence of the growing chains experience the same exchange in monomer concentrations (13). Lactones are present in a large variety of natural products and exhibit interesting biological properties (14). Natural insect feeding deterrents are one group of natural products considered to be useful tools to manipulate insect pest populations.…”
Section: Introductionmentioning
confidence: 99%