31456-25-4

Upstream product

• 53604-92-5 4-ethyl-6-formyl-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione 
• 55857-35-7 (E)-N-(2-aminobenzylidene)-4-methylaniline 
• 102978-40-5 4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 529-23-7 o-aminobenzaldehyde 
• 34086-64-1 2,3-dihydro-1H-pyrrolo[3,4-b]quinoline 
• 36625-47-5 methyl α-(tetrahydro-2-pyrrolidinylidene)acetate 
• 34141-34-9 9,11-dihydro-α-ethyl-9-oxoindolizino<1,2-b>quinoline-7-acetic acid, methyl ester 
• 38854-13-6 [1-(2-methoxycarbonyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-3-ylmethyl)-2-oxo-butyl]-malonic acid dimethyl ester 
• 38753-16-1 (8-ethoxycarbonyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-malonic acid di-tert-butyl ester 
• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 
• 80231-40-9 2-iodo-3-quinolinecarboxaldehyde 
• 127452-30-6 6-(acetamidomethyl)-1,1-(ethylenedioxy)-7-<1'-(ethoxycarbonyl)propyl>-5-oxo-Δ⁶⁽⁸⁾-tetrahydroindolizine 
• 58610-64-3 7’-methyl-5’-oxo-3’,5’-dihydro-2’H-spiro[[1,3]dioxolane-2,1‘-indolizine]-6’-carbonitrile 

Downstream Products

• 55854-89-2 8-methyl-7-propionylindolizino[1,2-b]quinoline-9(11H)-one 

Relevant academic research and scientific papers

A Six-Step Synthesis of (+/-)-Camptothecin

A six-step synthesis of (+/-)-camptothecin has been achieved starting from 2-methoxypyridine and 2-bromoquinoline.

A Concise Total Synthesis of (±)-Camptothecin

A total synthesis of racemic camptothecin, characterized by a concise construction of the ring systems and easy functional group transformation, is described. A domino reaction consisting of a Heck reaction and an aza-intramolecular Michael addition to form the C ring serves as the first key step in the synthesis. The D ring was constructed by a simple Wittig-Horner reaction followed by removal of the protective groups. Hydroxymethylation, demethylation, and lactone formation reactions were performed in one-pot to construct the E ring under hydrobromic acid conditions. This work provides an efficient scheme for further synthetic exploration of camptothecin and its analogues.

Plant antitumor agents: Synthesis and biological activity of camptothecin analogues

Four analogues, 10-methoxy (20), 12-aza (29), benz[j] (36), and 18-methoxy (38), of camptothecin were obtained by total synthesis. The two water-soluble analogues, 10-[(carboxymethyl)oxy] (24) and 10-[2'-(diethylamino)-ethoxy]-20(S)-camptothecin (26), wit

Copper(I) iodide-promoted hydroxylation onto the lithium or potassium enolate of lactones and lactams

After enolization of lactones (1a,b) and lactams (2a,b) with lithium or potassium hexamethyldisilazide in THF, each resultant enolate was treated with a solution prepared by mixing copper(I) iodide, pyridine, and tert-butyl hydroperoxide or N-methylmorpho

A novel, expeditious synthesis of racemic camptothecin

(Chemical Equation Presented) A novel and efficient synthesis of racemic camptothecin, starting from a readily accessible hydroxy pyridone, is presented. Key steps include a Claisen rearrangement of a functionalized allylic ether, a hindered Heck coupling

Synthesis of indolizinoquinolinones through three- and four-component domino Knoevenagel / hetero-Diels–Alder reactions: novel access to (+)-camptothecin

[Figure not available: see fulltext.] The fused heterocyclic indolizinoquinolinone system is a key structural feature of several highly bioactive alkaloids, including camptothecin. Camptothecin has been efficiently obtained by a three- or four-component domino Knoevenagel / hetero-Diels–Alder reaction of aldehyde, Meldrum's acid, and enol ether in the presence or absence of alcohol, followed by reductive cleavage of the amine protecting group. The obtained products were further transformed along several different routes leading to camptothecin.

Synthesis of (±)-camptothecin using a [3+2] nitrone cycloaddition to construct the CDE ring moiety

A novel synthesis to camptothecin is described. A Friedlander condensation of o-aminobenzaldehye with tricylclic ketone affords camptothecin after further elaboration. Tricyclic ketone is prepared via a route employing a [3+2] nitrone cycloaddition and an intramolecular Knoevenagel condensation. A novel synthesis to camptothecin is described. A Friedlander condensation of o-aminobenzaldehye 2 with tricylclic ketone 3 affords camptothecin after further elaboration. Tricyclic ketone 3 is prepared via a route employing a [3+2] nitrone cycloaddition and an intramolecular Knoevenagel condensation.

7-Substituted camptothecin and camptothecin analogs and methods for producing the same

Methods of forming camptothecin compounds which are effective anti-tumor compounds are disclosed. These compounds inhibit the enzyme topoisomerase I and may alkylate DNA of the associated topoisomerase I-DNA cleavable complex.

Biogenetically patterned synthesis of camptothecin and 20- deoxycamptothecin

A biogenetically patterned synthetic route to the monoterpenoid quinoline alkaloids 20-deoxycamptothecin and (±)-camptothecin from secologanin and tryptamine via vincoside/strictosidine lactams has now been realized, and hence afforded likely biosynthetic intermediates for testing in vivo. (C) 2000 Elsevier Science Ltd.

A practical and efficient synthesis of (±)- camptothecin

A practical and efficient synthesis of (±)-camptothecin from glycine via an intramolecular Michael addition is described.