(2aR,4aS,5aβ,8aα,8bβ,8cβ)-Decahydro-4bβ-methyl-8-methylene-7H-cyclobuta[1,4]cyclobuta[1,2,3-cd]furo[2,3-g]benzofuran-2,7-dione

Base Information

Chemical Name:(2aR,4aS,5aβ,8aα,8bβ,8cβ)-Decahydro-4bβ-methyl-8-methylene-7H-cyclobuta[1,4]cyclobuta[1,2,3-cd]furo[2,3-g]benzofuran-2,7-dione
CAS No.:27548-70-5
Molecular Formula:C₁₅H₁₆O₄
Molecular Weight:260.29
Hs Code.:
Mol file:27548-70-5.mol

Synonyms:2H,7H-Cyclobuta[1,4]cyclobuta[1,2,3-cd]furo[2,3-g]benzofuran-2,7-dione,3,4,4aa,4b,5,5ab,8,8aa,8bb,8cb-decahydro-4bb-methyl-8-methylene- (8CI);2H,7H-Cyclobuta[1,4]cyclobuta[1,2,3-cd]furo[2,3-g]benzofuran-2,7-dione,decahydro-4b-methyl-8-methylene-, [4aS-(2aS*,4aa,4bb,5ab,8aa,8bb,8cb)]-; Photoisabelin

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Chemical Property of (2aR,4aS,5aβ,8aα,8bβ,8cβ)-Decahydro-4bβ-methyl-8-methylene-7H-cyclobuta[1,4]cyclobuta[1,2,3-cd]furo[2,3-g]benzofuran-2,7-dione

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Technology Process of (2aR,4aS,5aβ,8aα,8bβ,8cβ)-Decahydro-4bβ-methyl-8-methylene-7H-cyclobuta[1,4]cyclobuta[1,2,3-cd]furo[2,3-g]benzofuran-2,7-dione

There total 9 articles about (2aR,4aS,5aβ,8aα,8bβ,8cβ)-Decahydro-4bβ-methyl-8-methylene-7H-cyclobuta[1,4]cyclobuta[1,2,3-cd]furo[2,3-g]benzofuran-2,7-dione 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:

: 72360-77-1,83150-81-6
(1S,2R,5S,6S)-6-Methyl-10-oxo-tricyclo[4.4.0.0^2,5]decane-2-carboxylic acid methyl ester

: 27548-70-5,75363-37-0
photoisabelin

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) LiN(i-Pr)2 / 1.) THF, -78 deg C

2: Pd(OAc)2 / acetonitrile / 24 h / 22 °C

3: 1.) NaBH₄, CeCl₃*xH₂O, 1 N HCl, 2.) p-TsOH*H₂O / 1.) methanol, 0 deg C, 10 min, 2.) C₆H₆, 22 deg C, 15 min

4: NBS / H₂O; 1,2-dimethoxy-ethane / 8 h / 22 °C

6: 1.) (CH₃)2CuLi, 2.) NH₄Cl / 1.) HMPA, Et₂O, -25 deg C, 2.) -20 deg C

7: 1.) NaBH₄, 2.) HCl / 1.) methanol, -10 deg C, 0.5 h, 2.) 22 deg C, 1 h

9: 1.) LiN(i-Pr)2, CH₂N(CH₃)2⁺I_-, 2.) Na₂CO₃ / 1.) THF, -60 deg C, 2.) THF, MeOH, CH₂Cl₂, H₂O

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; eschenmoser's salt; sodium carbonate; ammonium chloride; toluene-4-sulfonic acid; dimethylcopper lithium; lithium diisopropyl amide; In 1,2-dimethoxyethane; water; acetonitrile;
DOI:10.1021/ja00540a029

Reference yield:

: 72390-55-7,75363-35-8
(1S,2R,5S,6S)-6-Methyl-10-oxo-tricyclo[4.4.0.0^2,5]dec-8-ene-2-carboxylic acid methyl ester

: 27548-70-5,75363-37-0
photoisabelin

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaBH₄, CeCl₃*xH₂O, 1 N HCl, 2.) p-TsOH*H₂O / 1.) methanol, 0 deg C, 10 min, 2.) C₆H₆, 22 deg C, 15 min

2: NBS / H₂O; 1,2-dimethoxy-ethane / 8 h / 22 °C

4: 1.) (CH₃)2CuLi, 2.) NH₄Cl / 1.) HMPA, Et₂O, -25 deg C, 2.) -20 deg C

5: 1.) NaBH₄, 2.) HCl / 1.) methanol, -10 deg C, 0.5 h, 2.) 22 deg C, 1 h

7: 1.) LiN(i-Pr)2, CH₂N(CH₃)2⁺I_-, 2.) Na₂CO₃ / 1.) THF, -60 deg C, 2.) THF, MeOH, CH₂Cl₂, H₂O

With hydrogenchloride; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; eschenmoser's salt; sodium carbonate; ammonium chloride; toluene-4-sulfonic acid; dimethylcopper lithium; lithium diisopropyl amide; In 1,2-dimethoxyethane; water;
DOI:10.1021/ja00540a029

Reference yield:

: 72390-51-3
(1S,2R,5S,6S)-6-Methyl-10-trimethylsilanyloxy-tricyclo[4.4.0.0^2,5]dec-9-ene-2-carboxylic acid methyl ester

: 27548-70-5,75363-37-0
photoisabelin

Guidance literature:: Multi-step reaction with 8 steps

1: Pd(OAc)2 / acetonitrile / 24 h / 22 °C

2: 1.) NaBH₄, CeCl₃*xH₂O, 1 N HCl, 2.) p-TsOH*H₂O / 1.) methanol, 0 deg C, 10 min, 2.) C₆H₆, 22 deg C, 15 min

3: NBS / H₂O; 1,2-dimethoxy-ethane / 8 h / 22 °C

5: 1.) (CH₃)2CuLi, 2.) NH₄Cl / 1.) HMPA, Et₂O, -25 deg C, 2.) -20 deg C

6: 1.) NaBH₄, 2.) HCl / 1.) methanol, -10 deg C, 0.5 h, 2.) 22 deg C, 1 h

8: 1.) LiN(i-Pr)2, CH₂N(CH₃)2⁺I_-, 2.) Na₂CO₃ / 1.) THF, -60 deg C, 2.) THF, MeOH, CH₂Cl₂, H₂O

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; eschenmoser's salt; sodium carbonate; ammonium chloride; toluene-4-sulfonic acid; dimethylcopper lithium; lithium diisopropyl amide; In 1,2-dimethoxyethane; water; acetonitrile;
DOI:10.1021/ja00540a029