(2aR,2a⁽¹⁾R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

Base Information

• Chemical Name: (2aR,2a⁽¹⁾R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate
• CAS No.: 1384835-08-8
• Molecular Formula: C₂₇H₃₅NO₇
• Molecular Weight: 485.577

Synonyms:(2aR,2a⁽¹⁾R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

Chemical Property of (2aR,2a⁽¹⁾R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

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Technology Process of (2aR,2a⁽¹⁾R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

There total 9 articles about (2aR,2a⁽¹⁾R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate 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: 50.0%

2-(((methoxycarbonyl) ((1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-en-1-yl)amino)methyl)-3-oxocyclopent-1-en-1-yl acetate (1384835-07-7) → (2aR,2a(1)R,6aS,8R,9aR)methyl 8-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyl-3,6-dioxododecahydro-1H-cyclohepta[cd]indole-1-carboxylate (1384835-09-9) + (2aR,2a(1)R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate (1384835-08-8)

Guidance literature:

In acetonitrile; at 0 ℃; for 0.25h; Inert atmosphere; UV-irradiation;

DOI:10.1021/jo300776d

Reference yield:

(1S,5S)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enol (1384835-01-1) → (2aR,2a(1)R,6aS,8R,9aR)methyl 8-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyl-3,6-dioxododecahydro-1H-cyclohepta[cd]indole-1-carboxylate (1384835-09-9) + (2aR,2a(1)R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate (1384835-08-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.67 h / 0 °C / Inert atmosphere

1.2: 6 h / Reflux; Inert atmosphere

2.1: toluene-4-sulfonic acid / methanol; N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere

2.2: 4 h / 150 °C / Inert atmosphere

3.1: potassium tert-butylate / tert-butyl alcohol / 1.5 h / 20 °C / Inert atmosphere

4.1: Sn(NTf₂)4*9DMSO / acetonitrile / 4 h / 20 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

6.1: acetonitrile / 0.25 h / 0 °C / Inert atmosphere; UV-irradiation

With Sn(NTf₂)4*9DMSO; potassium tert-butylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Overman rearrangement / 1.2: Overman rearrangement;

DOI:10.1021/jo300776d

Reference yield:

2,2,2-trichloro-N-((1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)acetamide (1384835-03-3) → (2aR,2a(1)R,6aS,8R,9aR)methyl 8-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyl-3,6-dioxododecahydro-1H-cyclohepta[cd]indole-1-carboxylate (1384835-09-9) + (2aR,2a(1)R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate (1384835-08-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / methanol; N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere

1.2: 4 h / 150 °C / Inert atmosphere

2.1: potassium tert-butylate / tert-butyl alcohol / 1.5 h / 20 °C / Inert atmosphere

3.1: Sn(NTf₂)4*9DMSO / acetonitrile / 4 h / 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

5.1: acetonitrile / 0.25 h / 0 °C / Inert atmosphere; UV-irradiation

With Sn(NTf₂)4*9DMSO; potassium tert-butylate; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo300776d

upstream raw materials:

C₁₇H₂₄O₄S

(1S,5S)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enol

2,2,2-trichloro-N-((1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)acetamide

methyl (1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enylcarbamate

Downstream raw materials:

(2aR,2a⁽¹⁾R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

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