lycorane

Base Information

• Chemical Name: lycorane
• CAS No.: 6871-58-5
• Molecular Weight: 257.33
• Mol file: 6871-58-5.mol

Synonyms:lycorane;(12β,15β,16β)-9,10-(Methylenebisoxy)galanthan;(12β,15β,16β)-9,10-[Methylenebis(oxy)]galanthan;(12β,16β)-9,10-[Methylenebis(oxy)]galanthan;3aβ,12cβ-Lycoran;γ-Lycoran

Chemical Property of lycorane

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

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Technology Process of lycorane

There total 70 articles about lycorane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(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 (162600-14-8) → (+)-γ-lycorane (6871-58-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 18h; Heating;

DOI:10.1021/ol051795n DOI:10.1002/ejoc.200600275

Reference yield: 85.0%

(12α,15α,16α)-9,10-[methylenebis(oxy)]galanthan-7-one (287716-45-4) → (+)-γ-lycorane (6871-58-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1021/jo991791u

Reference yield: 82.0%

(2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone (1448847-29-7) → (+)-γ-lycorane (6871-58-5)

Guidance literature:

(2S,6R)-2-(6-((tert-butoxycarbonylamino)methyl)benzo[d][1,3]dioxol-5-yl)-6-(2-oxoethyl)cyclohexanone; With trifluoroacetic acid; In dichloromethane; at -10 ℃; for 2h;

With sodium tris(acetoxy)borohydride; In ethanol; at -10 ℃; for 3h;

DOI:10.1002/anie.201207561

upstream raw materials:

ent-9,10-methanediyldioxy-(16β)-galanth-1(15)-ene

(12α,15α,16α)-9,10-[methylenebis(oxy)]galanthan-7-one

(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

(S)-6-(3,4-methylenedioxyphenyl)-1-nitrocyclohexene

Refernces

ANODIC INTRAMOLECULAR ARYLATION OF ENAMINONES

10.1016/S0040-4039(01)91108-6

The study investigates the anodic intramolecular arylation of enaminones to produce isoquinolines and benzazepines. Enaminones, which are prepared by condensation of various benzylamines, phenethylamines, and anilines with 1,3-diketones, serve as the key substrates. The anodic oxidation potentials of these enaminones are measured and listed in Table 1. The preparative electrolyses of enaminones 1, 3 - 5 lead to the formation of isoquinolines and benzazepines in fair yields, as shown in Table 2. The anode potentials for these reactions range from +0.8 to +1.6 V vs. s.c.e. The study also notes that enaminone k does not cyclize under the given conditions but forms the iminoquinone ketal 11 instead. The anode reaction described provides a convenient one-step preparation of isoquinolines and benzazepines, which are suitable intermediates for the synthesis of various alkaloids such as lycorane, Cephalotaxus, and erythrina alkaloids.

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