(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates

Base Information

• Chemical Name: (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates
• CAS No.: 219650-31-4
• Molecular Formula: C₂₁H₂₂N₂O₄
• Molecular Weight: 366.417
• Mol file: 219650-31-4.mol

Synonyms:(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates

Chemical Property of (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates

There total 1 articles about (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates 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: 64.0%

Methyl diethylphosphonoacetate (1067-74-9) + (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-oxo-1H-pyrrolo-<2,3-d>carbazole-6-carboxylate (219650-29-0) → diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates (219650-31-4) + (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(Z)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates (219650-30-3)

Guidance literature:

With potassium hexamethyldisilazane; In tetrahydrofuran; for 0.5h; Yield given; Ambient temperature;

DOI:10.1021/jo9813989

Reference yield:

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates (219650-31-4) → strychnidin-10-one (57-24-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / DIBALH, BF₃*Et₂O / CH₂Cl₂ / 3 h / -78 °C

2: NaCNBH₃ / acetic acid / 0.5 h / 10 °C

3: 37 mg / NaOMe / methanol; tetrahydrofuran / 2 h / Ambient temperature

4: 71 percent / DIBALH / CH₂Cl₂ / 0.5 h / -90 °C

5: 65 percent / Ac₂O, NaOAc / acetic acid

With boron trifluoride diethyl etherate; sodium methylate; sodium acetate; acetic anhydride; diisobutylaluminium hydride; sodium cyanoborohydride; In tetrahydrofuran; methanol; dichloromethane; acetic acid;

DOI:10.1021/jo9813989

Reference yield:

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates (219650-31-4) → (17R,19E)-17,18-epoxy-cur-19-en-17-ol (466-85-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / DIBALH, BF₃*Et₂O / CH₂Cl₂ / 3 h / -78 °C

2: NaCNBH₃ / acetic acid / 0.5 h / 10 °C

3: 37 mg / NaOMe / methanol; tetrahydrofuran / 2 h / Ambient temperature

4: 71 percent / DIBALH / CH₂Cl₂ / 0.5 h / -90 °C

With boron trifluoride diethyl etherate; sodium methylate; diisobutylaluminium hydride; sodium cyanoborohydride; In tetrahydrofuran; methanol; dichloromethane; acetic acid;

DOI:10.1021/jo9813989

upstream raw materials:

Methyl diethylphosphonoacetate

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-oxo-1H-pyrrolo-<2,3-d>carbazole-6-carboxylate

Downstream raw materials:

(17R,19E)-17,18-epoxy-cur-19-en-17-ol

strychnidin-10-one

Refernces