- Suppression of β-hydride elimination in the intramolecular hydrocarboxylation of alkynes leading to the formation of lactones
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Palladium-catalyzed intramolecular cyclization of the alkynoic acids was studied which gave the five- and six-membered lactones in moderate yields. The reaction can be conducted simply by heating a toluene solution of alkynoic acids at 100 °C in the prese
- Huo, Zhibao,Patil, Nitin T.,Jin, Tienan,Pahadi, Nirmal K.,Yamamoto, Yoshinori
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- γ-substituted butanolides from cyclopropane hemimalonates: An expedient synthesis of natural (R)-dodecan-4-olide
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Exploration into the reactivity of donor-acceptor cyclopropane hemimalonates has led to the facile synthesis of γ-substituted butanolides. Under microwave irradiation, cyclopropane hemimalonates undergo rapid conversion to butanolides in the presence of i
- Grover, Huck K.,Emmett, Michael R.,Kerr, Michael A.
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supporting information
p. 4838 - 4841
(2013/10/08)
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- Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs
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A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5- (hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC 50 = 12 μM). Structure-activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.
- Mohideen, Mazlin,Zulkepli, Suraya,Nik-Salleh, Nik-Salmah,Zulkefeli, Mohd,Weber, Jean-Frédéric Faizal Abdullah,Rahman, A. F. M. Motiur
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p. 812 - 831
(2013/07/26)
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- Divergent synthetic routes for ring expansion or cyclization from 1,4-allylic diol derivatives via gold(I) catalysis or zinc(II) mediation
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A new efficient method was developed to transform cyclic alkanols into one-carbon higher homologated ketones using various esters as the leaving groups through gold-catalyzed allylic cation-promoted pinacol-type rearrangement. This reaction, coupled with
- Zhu, Li-Li,Li, Xiao-Xiao,Zhou, Wen,Li, Xin,Chen, Zili
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scheme or table
p. 8814 - 8823
(2011/12/22)
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- Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids
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γ- and δ-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3, 4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid; the δ-lactones ware always obtained in an ee% higher than the γ-lactones and ranging from 70% to 100%.
- Aquino, Mario,Cardani, Silvia,Fronza, Giovanni,Fuganti, Claudio,Fernandez, Rosalino Pulido,Tagliani, Auro
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p. 7887 - 7896
(2007/10/02)
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- 3,3-Diethoxypropyl-lithium: A Masked Lithium Propanal Homoenolate in Organic Synthesis
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3,3-Diethoxypropyl-lithium is prepared by lithiation of the corresponding chlorinated precursor with lithium naphthalenide at -78 deg C; the reaction of this masked propanal homoenolate with different elctrophilic reagents CO, (CH2)7CO, PhCOMe, PhCH=NPh, PhCONEt2, PhCN, c-C6H11CN, 4-MeC6H4CN> leads to the corresponding mono- and bi-functionalized compounds.In the case of the reaction with aldehydes or ketones the prepared crude products are oxidized with m-chloroperbenzoic acid, yielding directly the γ-substituted butyrolactones.
- Barluenga, Jose,Fernandez, Jose R.,Rubiera, Covadonga,Yus, Miguel
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p. 3113 - 3118
(2007/10/02)
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- SYNTHESIS OF VINYLIC LACTONES VIA PALLADIUM-CATALYZED COUPLING OF VINYLIC HALIDES OR TRIFLATES AND UNSATURATED CARBOXYLIC ACIDS
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Vinylic halides or triflates react with 3-butenoic or 4-pentenoic acids in the presence of 5percent Pd(OAc)2 or Pd(dba)2, n-Bu4NCl, i-PrNEt and either acetonitrile or N,N-dimethylformamide at 80-100 deg C to afford the corresponding γ-alkenyl-γ-butyro- or
- Larock, Richard C.,Leuck, David J.,Harrison, L. Wayne
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p. 6399 - 6402
(2007/10/02)
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