87302-53-2

Upstream product

• 108-55-4 glutaric anhydride, 
• 906534-14-3 (9R,9aR)-3,6,7-Trimethoxy-9,10,11,12,13,14-hexahydro-9aH-13a-aza-benzo[b]triphenylen-9-ol 
• 87302-60-1 (15S)-15-hydroxy-2,3,6-trimethoxyphenanthro<9,10-b>quinolizidine 
• 1217508-57-0 C₂₄H₂₅NO₄ 
• 585573-79-1 10-(bromomethyl)-2,3,6-trimethoxyphenanthrene 
• 50-00-0 formaldehyd 
• 697234-86-9 (R)-2-((2,3,6-trimethoxyphenanthren-10-yl)methyl)piperidine 
• 162869-95-6 11,12,13,14,14a,15-Hexahydro-2,3,6-trimethoxy-9H-phenanthro<9,10-b>quinolizin-9-one 
• 20772-34-3 (S)-4,6,7,8,9,9a-hexahydro-2-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-1H-quinolizine 
• 1394132-10-5 (S)-2,3,9,9a-tetrahydro-8-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one 
• 1394132-09-2 (S)-4,6,7,8,9,9a-hexahydro-3-(4-methoxyphenyl)-6-oxo-1H-quinolizin-2-yl trifluoromethanesulfonate 
• 1394132-08-1 (3R,9aS)-hexahydro-3-(4-methoxyphenyl)-1H-quinolizine-2,6-dione 
• 1394132-07-0 (7R,8S,9aS)-hexahydro-8-hydroxy-7-(4-methoxyphenyl)-1H-quinolizin-4(6H)-one 
• 1394132-12-7 methyl 4-((2S,4S,5R)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoate 

Relevant academic research and scientific papers

Total Synthesis of Cryptopleurine and Its Analogues

Total synthesis of phenanthroquinolizidine alkaloid cryptopleurine was achieved in 8 steps from commercially available 2-pyridinecarboxaldehyde and the epoxide derived from methyleugenol. The key intermediate vinyl triflate enables the divergent synthesis of cryptopleurine derivatives by late-stage installation of various substituents on the C-ring.

Synthesis of (-)-cryptopleurine by combining gold(I) catalysis with a free radical cyclization

(R)-(-)-Cryptopleurine, a highly cytotoxic alkaloid found in Cryptocarya and Boehmeria species, was synthesized in high optical purity using a gold(I)-NHC catalyzed cyclization of an unsymmetrical phenanthrene precursor combined with a free radical cyclization to achieve closure of the C-ring.

Antofine and cryptopleurine derivatives as anticancer agents

The present invention provides compounds of Formula (I-IV): compositions containing the same, and methods of use thereof such as for the treatment of cancer.

Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs

(-)-Cryptopleurine 1 is one of the most potent anti-proliferative member of the phenanthroquinolizidine class of alkaloids. We report here the synthesis of (-)-6-O-desmethylcryptopleurine (-)-2 and (-)-6-O-desmethyl-(15R)-hydroxycryptopleurine (-)-4 in th

Collective asymmetric synthesis of (-)-Antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert- butanesulfinamide as a chiral auxiliary

A collective asymmetric synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine was achieved by means of a reaction sequence involving efficient generation of chiral homoallylic amine intermediates by asymmetric allylation of the corresponding tert-butanesulfinyl imine. From these intermediates, the pyrrolidine and piperidine rings were constructed by means of an intramolecular SN2 substitution reaction and a ring-closing metathesis reaction, respectively. The unusual C5-methoxy-substituted phenanthrene moiety of (-)-tylocrebrine was generated by means of an InCl3-catalyzed cycloisomerization reaction of an o-propargylbiaryl compound.

Total synthesis of (+)-antofine and (-)-cryptopleurine

The tylophorine alkaloid anticancer compounds antofine and cryptopleurine have been synthesized in optically active form. Both syntheses use optically pure α-amino acids as the starting materials, require only seven steps from known 2-ethynylpyrrolidine or 2-ethynylpiperidine derivatives, and are free of protecting groups. The key steps include an alkyne hydration and a chromium-carbene-complex-based net [5 + 5]-cycloaddition step. The alkyne hydration was accompanied by racemization of the β-amino ketone product under most of the conditions examined, and minimization of this side-reaction was achieved through careful pH control and choice of metal additive. The final ring closure involved a Bischler-Napieralski reaction using a carbamate (antofine) or urea (cryptopleurine) precursor. Single enantiomers of the tylophorine alkaloids antofine and cryptopleurine have been prepared by using a short synthesis that involves regioselective alkyne hydration of a chiral propargylic amide, Fischer carbene complex mediated net [5+5] cycloaddition, and urea-based Friedel-Crafts acylation as key steps. Copyright

Enantioselective approach to functionalized quinolizidines: Synthesis of (+)-julandine and (+)-cryptopleurine

An efficient synthesis of functionalized quinolizidines was developed from an enantiomerically enriched γ-nitroketone, which is easily prepared by an organocatalytic ketone-nitroalkene Michael addition. Oxidative ring expansion of the nitroketone followed

Enantioselective synthesis of cryptopleurine and boehmeriasin A via organocatalytic intramolecular aza-Michael addition

The enantioselective synthesis of phenanthroquinolizidine alkaloids cryptopleurine and boehmeriasin A was achieved in eight steps from commercial available Cbz-protected 2-piperidinone in 22% and 20% overall yield, respectively. The key steps of this route are intramolecular enantioselective aza-Michael addition, intramolecular aldol addition, and oxidative coupling.

Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues

Chemical equation presented A new versatile synthetic methodology for the synthesis of enantiomerically pure natural phenanthroindolizidines and phenanthroquinolizidines has been established and described. Natural products R-antofine and R-cryptopleurine, as well as a novel E-ring expanded analogue 13c (E7), 12-oxo-S-antofine (17), and 12N-methyl-12-aza-S-antofine (18) were synthesized with the new method. This strategy will greatly facilitate future SAR studies on the natural alkaloids with E-ring variations.

Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation

A concise and efficient route involving Parham-type cycliacylation as the key step has been used to synthesize phenanthroquinolizidine alkaloids 1a-c and 2a-c. Among the products, 1b-(S), 1b-(R), 2a-(14aS,15S), 2a-(14aR,15R), and 2b were synthesized for the first time.