476-33-5

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Uses

Homochelidonine is pharmaceutical compound comprising alkaloids and non-alkaloid components.

InChI:InChI=1/C21H23NO5/c1-22-9-14-12(4-5-16(24-2)21(14)25-3)19-15(23)6-11-7-17-18(27-10-26-17)8-13(11)20(19)22/h4-5,7-8,15,19-20,23H,6,9-10H2,1-3H3/t15-,19-,20+/m0/s1

Upstream product

• 929189-28-6 benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate 
• 929189-24-2 benzyl (5S,6R)-6-(3,4-dimethoxy-2-((methoxymethoxy)methyl)phenyl)-5,6-dihydronaphtho[2,3-d][1,3]dioxol-5-ylcarbamate 
• 929189-25-3 benzyl (5S,6R)-6-[2-(hydroxymethyl)-3,4-dimethoxyphenyl]-5,6-dihydronaphtho[2,3-d][1,3]dioxol-5-ylcarbamate 
• 929189-26-4 benzyl (4bR,11bS)-1,2-dimethoxy-4b,13-dihydro[1,3]benzodioxolo[5,6-c]phenanthridine-12(11bH)-carboxylate 
• 929189-27-5 benzyl (4bR,5S,6S,11bS)-5-bromo-6-hydroxy-1,2-dimethoxy-4b,6,11b,13-tetrahydro[1,3]benzodioxolo[5,6-c]phenanthridine-12(5H)-carboxylate 
• 5653-67-8 2,3-dimethoxybenzyl alcohol 
• 107290-27-7 (6-bromo-2,3-dimethoxyphenyl)methanol 
• 220956-31-0 1-bromo-3,4-dimethoxy-2-((methoxymethoxy)methyl)benzene 
• 220956-32-1 3,4-dimethoxy-2-(methoxymethoxy)methylphenylboronic acid 
• 65910-39-6 1,2,6ξ-trimethoxy-12-methyl-(4br,11bc)-4b,5,6,11b,12,13-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-5t-ol 
• 65910-36-3 12-hydroxy-homochelidonine 
• 65910-39-6 (4bα,10bα,11β)-4b,5,6,10b,11,12-hexahydro-7,8,12-trimethoxy-5-methyl-2,3-methylenedioxybenzophenanthridine-11-ol 
• 164524-89-4 3,4-dehydro-6,7-methylenedioxy-1-tetralone-2-spiro-3'-(6,7-dimethoxyphthalide) 

Relevant academic research and scientific papers

Stereoselective total synthesis of (±)-homochelidonine

(±)-Homochelidonine, a B/C-cis-11-hydroxyhexahydrobenzo[c]phenanthridine alkaloid, was stereoselectively synthesized from arnottin II, a non-alkaloidal spirolactonyl tetralone which had been structurally correlated to chelerythrine, a fully aromatized-type alkaloid, by the common use of a 2-benzofuranyl-1-tetralone as a synthetic key intermediate. Thus, a valuable synthetic method accessible to benzo[c]phenanthridine alkaloids with different oxidation stages of the basic skeleton could be proposed.

Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a PdII-catalyzed ring-opening strategy

New enantioselective syntheses of the B/C hexahydrobenzo[c]phenanthridine alkaloids (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine, and (+)-norchelidonine are described. Our rapid and convergent route to this class of natural products involved the development and application of a Pd II-catalyzed asymmetric ring-opening reaction of a mesoazabicyclic alkene with an aryl boronic acid as the key step. By screening a variety of functionalized ortho-substituted aryl boronic acids, chiral ligands and reaction conditions we were able to prepare the requisite cis-1-amino-2- aryldihydronaphthalenes in high yield and in up to 90% ee. Early attempts to complete the synthesis of (+)-homochelidonine using an N-Boc azabicyclic alkene are described in full. The successful route required a protecting group alteration followed by B ring for-mation and then stereoselective installation of the C-11 syn-hydroxy group by regioselective epoxide ring-opening using a hydride source. Ring-opening of the same epoxide intermediate with water ultimately led to the synthesis of (+)-chelamidine. The same strategy was then used to synthesize the other structurally similar B/C hexahydrobenzo[c] phenanthridine alkaloids, (+)-chelidonine, (+)-chelamidine, and (+)norchelidonine.

Enantioselective total synthesis of (+)-homochelidonine by a Pd II-catalyzed asymmetric ring-opening reaction of a meso-azabicyclic alkene with an aryl boronic acid

(Chemical Equation Presented) An efficient and highly convergent enantioselective synthesis of (+)-homochelidonine has been achieved (see scheme; Cbz = benzyloxycarbonyl, MOM = methoxymethyl) and relied on a new and powerful desymmetrizing ring-opening reaction of a meso-azabicycle with an aryl boronic acid. The route should allow access to other hexahydrobenzo[c]phenanthridine alkaloids.

Photocyclisation of Enamides. Part 19. Total Synthesis of (+/-)-Homochelidonine

Photocyclisation of the enamide (2) and successive stereoselective functionalisation of the photocyclised didehydro lactam (3a) completed the first total synthesis of (+/-)-homochelidonine (7e).