Total synthesis of (+-)-camptothecin

Tang, Cyril; Rapoport, Henry

doi:10.1021/ja00779a073

Cited by 35 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Annelation reaction with heterocyclic aminoaldehydes provides synthetic entry into heterocyclic systems fused to a pyridine or pyrimidine (44)(45)(46)(47) nucleus by condensation reaction. o-Aminoaldehyde has fascinating potential, remarkable versatility and utility for the annelation of heterocyclic ring structures to synthesize various heterocycles (48)(49)(50)(51)(52)(53). Known 2-aminoquinoline-3-carbaldehyde (o-aminoaldehyde) 1 has been synthesized by a novel method reported in our previous communication (42).…”

Section: Resultsmentioning

confidence: 99%

Effects of homogeneous media, binary mixtures and microheterogeneous media on the fluorescence and fluorescence probe properties of some benzo[b][1,8]naphthyridiens with HSA and BSA

Shelar¹,

Rote²,

Patil³

et al. 2011

Luminescence

View full text Add to dashboard Cite

A rapid and efficient method for the synthesis of various poly-substituted benzo[b][1,8]naphthyridines in high yield has been developed via the Friedländer condensation of 2-aminoquinoline-3-carbaldehyde 1 with various alicyclic ketones in a base catalyst (aq. potassium hydroxide). A series of benzo[b][1,8]naphthyridines branched with various side-chains and substituents were prepared with the aim of being investigated as a fluorescent agents. Electronic absorption and fluorescence properties of some representative benzonaphthyridines (3d, 5b and 21f) in homogeneous organic solvents, dioxane-water binary mixtures and in the microheterogeneous media (sodium dodecyl sulphate (SDS), cetyl trimethyl ammonium bromide (CTAB) and Triton-X100 micelles) have been examined. A linear correlation between solvent polarity and fluorescence properties was observed. Further, the interaction of these benzonaphthyridines (3d, 5b and 21f) with human serum albumin (HSA) and bovine serum albumin (BSA) in phosphate buffer have been examined by UV-vis absorption and fluorescence spectroscopy. The fluorescence intensity of 3d, 5b and 21f increases with the increasing HSA and BSA concentration. These benzonaphthyridines also quench the 345 nm fluorescence of BSA in phosphate buffer (λ(ex) 280 nm). These compounds have potential for use as neutral and hydrophobic fluorescence probes for examining the microenvironments in proteins, polymers, micelles, etc.

show abstract

Section: Resultsmentioning

confidence: 99%

Effects of homogeneous media, binary mixtures and microheterogeneous media on the fluorescence and fluorescence probe properties of some benzo[b][1,8]naphthyridiens with HSA and BSA

Shelar¹,

Rote²,

Patil³

et al. 2011

Luminescence

View full text Add to dashboard Cite

show abstract

“…1 H NMR (300 MHz, CDCl 3 , 7.26 ppm): 0.06, 0.11, 0.25 and 0.28 ppm (Me 2 SiO ), 0.5 ppm (m, CH 2 CH 2 CH 2 Si, 4H), 1.63 ppm (m, CH 2 CH 2 CH 2 Si, 4H), 4.01 ppm (m, AcOCH 2 CH 2 CH 2 Si, 4H), CH 3 C O (s, 3H); 13 C NMR (77.0 MHz, CDCl 3 , 77.0 ppm): 0.22 ppm ((CH 3 ) 2 SiO ), 14.12 ppm (CH 2 CH 2 CH 2 Si), 21.00 ppm (CH 2 CH 2 CH 2 Si), 22.59 ppm (CH 3 CO 2 R), 66.94 ppm (AcOCH 2 CH 2 CH 2 ), 171.16 ppm (C O). De-acylation of bisacetate 3 was routinely carried out using an 8 fold excess of anhydrous MeOH and 20 mol% K 2 CO 3 for 2 h at room temperature to yield diol 4 in nearly 87-95% yield as a clear to straw coloured liquid [25]. 1 29 Si NMR (59.6 MHz, CDCl 3 , TMS): 7.28 ppm; EI-MS: (M + ) 250 m/z.…”

Section: Differential Scanning Calorimetry (Dsc)mentioning

confidence: 99%

Synthesis of polyesters containing disiloxane subunits: Structural characterization, kinetics, and an examination of the thermal tolerance of Novozym-435

Frampton

Séguin

Marquardt

et al. 2013

Journal of Molecular Catalysis B: Enzymatic

View full text Add to dashboard Cite

“…The Rapoport-Tang Synthesis-Two known reactions were of primary importance in this synthesis (33). First, the a-methylene-lactam rearrange-…”

Section: -( F ) -C a M P T O T H E C I N (I)mentioning

confidence: 99%

“…The Rapoport-Tang Synthesis-Two known reactions were of primary importance in this synthesis (33). First, the a-methylene-lactam rearrange- modification of the Claisen thermal rearrangement had been proven to be an efficient method for the preparation of substituted olefins.…”

Section: -( F ) -C a M P T O T H E C I N (I)mentioning

confidence: 99%