(+/-)-3-epi-8-oxoerysotrine

Base Information

• Chemical Name: (+/-)-3-epi-8-oxoerysotrine
• CAS No.: 112342-35-5
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38
• Mol file: 112342-35-5.mol

Synonyms:

Chemical Property of (+/-)-3-epi-8-oxoerysotrine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-3-epi-8-oxoerysotrine

There total 91 articles about (+/-)-3-epi-8-oxoerysotrine 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: 100.0%

(2R,13bS)-2-hydroxy-11,12-dimethoxy-8,9-dihydro-1H-indolo[7a,1-a]isoquinolin-6(2H)-one (81750-70-1,81753-00-6,141987-93-1) + methyl iodide (74-88-4) → (+/-)-3α,15,16-trimethoxy-8-oxo-Δ1,6-erythrinan (52358-58-4,69111-35-9,112342-35-5)

Guidance literature:

With potassium hydroxide; tetraethylammonium bromide; In ethyl acetate; at 20 ℃; for 48h;

DOI:10.1039/b001906m

Reference yield: 91.0%

(3S*,5R*)-3-hydroxy-15,16-dimethoxy-8-oxoerythrina-1,6-diene (81750-70-1,81753-00-6,141987-93-1) + methyl iodide (74-88-4) → (+/-)-3-epi-8-oxoerysotrine (52358-58-4,69111-35-9,112342-35-5)

Guidance literature:

With sodium hydroxide; tetraethylammonium bromide; In tetrahydrofuran; at 20 ℃; for 36h;

DOI:10.1021/ol0607185

Reference yield:

11,12-dimethoxy-1,2,8,9-tetrahydroindolo[7a,1-a]isoquinolin-6-one (125226-18-8) → (+/-)-3α,15,16-trimethoxy-8-oxo-Δ1,6-erythrinan (52358-58-4,69111-35-9,112342-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 15 percent / SeO₂ / dioxane / 168 h / Heating

2: 91 percent / NaOH; Et₄NBr / tetrahydrofuran / 36 h / 25 °C

With sodium hydroxide; selenium(IV) oxide; tetraethylammonium bromide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jo061269p

upstream raw materials:

diphenyl diselenide

3α,15,16-Trimethoxy-8-oxo-Δ¹-cis-erythrinan

(2R,13bS)-2-hydroxy-11,12-dimethoxy-8,9-dihydro-1H-indolo[7a,1-a]isoquinolin-6(2H)-one

methyl iodide

Downstream raw materials:

(+/-)-erysotrine

(+/-)-3-epierysotrine

(+)-erysotrine

11β-hydroxyerysotrine (erythrartine)

Refernces

• 1、 Lee, Hyoung Ik,Cassidy, Michael P,Rashatasakhon, Paitoon,Padwa, Albert. "Efficient synthesis of (+/-)-erysotramidine using an NBS-promoted cyclization reaction of a hexahydroindolinone derivative.". . p. 5067 - 5070. Retrieved 2003.
• 2、 Gao, Shuanhu,Tu, Yong Qiang,Hu, Xiangdong,Wang, Shaohua,Hua, Rongbao,Jiang, Yijun,Zhao, Yuming,Fan, Xiaohui,Zhang, Shuyu. "General and efficient strategy for erythrinan and homoerythrinan alkaloids: Syntheses of (±)-3-demethoxyerythratidinone and (±)- erysotramidine". . p. 2373 - 2376. Retrieved 2007/10/03.