Total synthesis of dl-camptothecin

Tang, Cyril; Morrow, Cary J.; Rapoport, Henry

doi:10.1021/ja00834a028

Cited by 55 publications

(8 citation statements)

References 16 publications

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

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

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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.

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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

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“…21 The methoxy carbonyl group of 12a was removed by reaction with lithium mercaptide in HMPA22 yielding 90% of 20(S) -camptothecin (12b) identical in every respect with natural material:23 found for synthetic 12b, [a]22D +31.1°(20% MeOH in CHCI3), mp 275-278°d ec; found for naturally derived camptothecin, [a]25D +31.3°(20% MeOH in CHCI3),1 mp 276-278°dec. 24 The NMR, ir, uv, TLC, MS, and mixture melting point all confirmed the identity of synthetic and natural camptothecins.25…”

mentioning

confidence: 74%

Total synthesis of natural 20(S)-camptothecin

Ej¹,

Dn²,

Je³

1975

J. Org. Chem.

107

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“…They permit easy accessibility of simple derivatives, provide them with exceptional versatility in heterocyclic annulations. From the literature, it was noted that o ‐amino benzaldehyde, the first and best‐known member of this class of compounds have been utilized for the synthesis of various heterocycles such as pyridine derivatives [1], quinoline compounds [2], benzo pyrano/thiopyrano quinoline derivatives [3,4], thieno‐quinolines [5], pyrollo‐quinolines [6], indozolino quinolines [7], anthrazolines [8], naphtyridine derivatives [9,10], and so forth. An annulation reaction of heterocyclic amino aldehyde provides a synthetic entry into heterocyclic systems fused to chromene [11], pyridine [12–15], pyrazole [16–19], and quinoline nucleus [20,21].…”

Section: Introductionmentioning

confidence: 99%

New synthetic strategy for Friedlander condensation of 4‐amino‐2‐oxo‐2H‐chromene‐3‐carbaldehyde by heterogeneous catalysis

Jadhav¹,

Medhane²,

Deshmukh³

et al. 2021

Journal of Heterocyclic Chem

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Chromenopyridines are an important class of compound because of their diverse biological activities. In the present work, we have developed convenient route for the synthesis of chromeno[4,3‐b] pyridine derivatives (3a–e, 5a–e, and 7a–d) by Friedlander condensation of 4‐amino‐2‐oxo‐2H‐chromene‐3‐carbaldehyde with various active methylene compounds. We have used mixed metal oxide catalyst such as nanomaterial Zinc titanate. The reaction was carried out for various solvent systems, also we have altered the concentration of the catalyst. The 2‐propanol/water solvent system and 5 mol% catalyst concentration are best as far as yield and rate of reaction are concerned. The structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectra, and elemental analysis.

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Total synthesis of dl-camptothecin

Cited by 55 publications

References 16 publications

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

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

Total synthesis of natural 20(S)-camptothecin

New synthetic strategy for Friedlander condensation of 4‐amino‐2‐oxo‐2H‐chromene‐3‐carbaldehyde by heterogeneous catalysis

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