6871-58-5

Upstream product

• 54022-57-0 ent-9,10-methanediyldioxy-(16β)-galanth-1(15)-ene 
• 14022-01-6 9,10-methanediyldioxy-(12β)-galanthan-1α-ol 
• 162600-14-8 (3aR,3a1S,12bS)-2,3,3a,4,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-5(3a1H)-one 
• 287716-45-4 (12α,15α,16α)-9,10-[methylenebis(oxy)]galanthan-7-one 
• 36066-90-7 4c-(toluene-4-sulfonyloxymethyl)-(4ar,11bc)-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 
• 36066-92-9 4c-(trichloroacetoxy-methyl)-(4ar,11bc)-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 
• 36066-88-3 (6-oxo-(4ar,11bc)-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-4c-yl)-acetic acid 
• 36066-89-4 (6-oxo-(4ar,11bc)-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-4c-yl)-acetonitrile 
• 36274-94-9 8c-hydroxymethyl-(4br,8ac)-4b,5,6,7,8,8a-hexahydro-fluoreno[2,3-d][1,3]dioxol-9-one 
• 36066-91-8 4c-hydroxymethyl-(4ar,11bc)-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 
• 36066-87-2 rac-9,10-methanediyldioxy-(16β)-galanthane-5,7-dione 

Relevant academic research and scientific papers

Total synthesis of (+)-γ-lycorane from ethyl lactate using iterative Claisen and Overman rearrangement reactions

Total synthesis of (+)-γ-lycorane is accomplished from (S)-ethyl lactate. Key disconnections in the synthesis involve an iterative Claisen and Overman rearrangement reactions to install the chiral centers in the tetrahydroindole moiety while, Pictet-Speng

Method for asymmetrically synthesizing lycoris alkaloid (+)-gamma-lycorane

The invention discloses a convenient and efficient method for asymmetrically synthesizing lycoris alkaloid (+)-gamma-lycorine. According to the method, a lactone compound (2) is used as an initial rawmaterial, and the lycoris alkaloid (+)-gamma-lycorane is prepared through six steps: a condensation reaction, a decarboxylation reaction, a reduction reaction, and the like. According to the method,the primary raw materials are cheap and easily available, the operation process is simple and convenient, the synthetic route is short, and good technical support is provided for realizing large-scaleproduction of lycorine series molecules and researching the structure-activity relationship.

Asymmetric hydrogenation of α,α′-disubstituted cycloketones through dynamic kinetic resolution: An efficient construction of chiral diols with three contiguous stereocenters

Chiral diols with three contiguous stereocenters were synthesized by a highly enantioselective ruthenium-catalyzed asymmetric hydrogenation of racemic α,α′-disubstituted cycloketones involving dynamic kinetic resolution. This new catalytic asymmetric method provides a concise route to the alkaloid (+)-γ-lycorane. Copyright

Novel synthetic approach to nine-membered diallylic amides: Stereochemical behavior and utility as chiral building block

An efficient approach to nine-membered diallylic cyclic amides having a variety of substituents has been developed. The synthesized amides have stable planar chirality at ambient temperature. The transformation of the enantiomerically enriched amides provides optically active compounds containing stereogenic centers in a stereospecific fashion. As a demonstration of the synthetic utility of the amides, we have synthesized (+)-γ-lycorane using such an optically active amide as a chiral building block. Georg Thieme Verlag Stuttgart.

Catalytic asymmetric transformations with fine-tunable biphenol-based monodentate ligands

A library of new fine-tunable monodentate phosphite and phosphoramidite ligands based on chiral biphenol have been designed and developed. These monodentate phosphorus ligands have exhibited excellent enantioselectivity in the Pd-catalyzed asymmetric allylic alkylation and Rh-catalyzed asymmetric hydrogenation.

Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation

A highly efficient short total synthesis of (+)-γ-lycorane (>99% ee, 41% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite l

Rhodium-catalyzed asymmetric nitroallylation of arylmetallics with cyclic nitroallyl acetates and applications in organic synthesis

Highly enantioselective rhodium-catalyzed nitroallylations of arylboronic acids and arylzinc chlorides with cyclic nitroallyl acetates are described. Catalyst screening indicated that the rhodium complex of [Rh(OH)(CODJ] 2 and optically pure bi

Asymmetric nitroallylation of arylboronic acids with nitroallyl acetates catalyzed by chiral rhodium complexes and its application in a concise total synthesis of optically pure (+)-γ-lycorane

(Chemical Equation Presented) A new rhodium-catalyzed highly enantioselective nitroallylation of 2-nitrocyclohex-2-enol esters with arylboronic acids is described. A rhodium complex of [RhOH(COD)]2 and optically pure BINAP is the optimal cataly

Electrocyclic ring-opening/π-allyl cation cyclization reaction sequences involving gem-dihalocyclopropanes as substrates: Application to syntheses of (±)-, (+)-, and (-)-γ-lycorane

The readily prepared gem-dibromocyclopropanes (±)-13 and (±)-19 each engage in a silver(I)-promoted electrocyclic ring-opening/π-allyl cation cyclization sequence to deliver the hexahydroindole (±)-20, which participates in a Suzuki cross-coupling reaction with arylboronic acid 3 to give the tetracyclic compound (±)-21. Catalytic hydrogenation of this last compound proceeds in a completely stereoselective manner to give the saturated analogue (±)-24, which undergoes Bischler-Napieralski cyclization on reaction with phosphorus oxychloride. The resulting lactam (±)-25 is then reduced with lithium aluminum hydride to give (±)-γ-lycorane [(±)-1]. By using (-)-menthyl-derived carbamates 27 and 28, this chemistry has been extended to the synthesis of the (+)- and (-)-modifications of the title compound.