[1S,1'S,4S,5R,(+)]-3',3'a,4',5',6',6'a-Hexahydro-1'α,3'aα,4'α,6'aα-tetramethylspiro[2,6-dioxabicyclo[3.1.0]hexane-4,2'(1'H)-pentalene]-3-one

Base Information

• Chemical Name: [1S,1'S,4S,5R,(+)]-3',3'a,4',5',6',6'a-Hexahydro-1'α,3'aα,4'α,6'aα-tetramethylspiro[2,6-dioxabicyclo[3.1.0]hexane-4,2'(1'H)-pentalene]-3-one
• CAS No.: 81674-82-0
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 81674-82-0.mol

Synonyms:

Chemical Property of [1S,1'S,4S,5R,(+)]-3',3'a,4',5',6',6'a-Hexahydro-1'α,3'aα,4'α,6'aα-tetramethylspiro[2,6-dioxabicyclo[3.1.0]hexane-4,2'(1'H)-pentalene]-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1S,1'S,4S,5R,(+)]-3',3'a,4',5',6',6'a-Hexahydro-1'α,3'aα,4'α,6'aα-tetramethylspiro[2,6-dioxabicyclo[3.1.0]hexane-4,2'(1'H)-pentalene]-3-one

There total 17 articles about [1S,1'S,4S,5R,(+)]-3',3'a,4',5',6',6'a-Hexahydro-1'α,3'aα,4'α,6'aα-tetramethylspiro[2,6-dioxabicyclo[3.1.0]hexane-4,2'(1'H)-pentalene]-3-one 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: 96.0%

(1RS,2RS,3RS,5RS,6SR)-1,2,5,6-tetramethylbicyclo<3.3.0>octane-3-spiro-5'-2'-oxacyclopent-3'-en-1'-one (88907-84-0,88930-70-5,116297-22-4) → isoptychanolide (81674-82-0,89015-22-5,108646-50-0)

Guidance literature:

In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87670-5

Reference yield:

(1r,2RS,5SR)-trimethylcyclopentane-1-carboxylic acid (88907-88-4) → isoptychanolide (81674-82-0,89015-22-5,108646-50-0)

Guidance literature:

Multi-step reaction with 14 steps

1: SOCl₂

2: 1.) AlCl₃, 2.) Na₂B₄O₇ / 1.) CH₂Cl₂, 2.) aq. MeOH, pH= 8.5

3: 76 percent / 6 h / 620 °C / 14 Torr

4: 1.) CuI / 1.) diethylether, -30 deg C, 15 min; 2.) diethylether, -30 to 0 deg C, 3 h, 3.) diethylether, -60 deg C, 90 min.

5: diethyl ether

6: 1.) NaH / 1.) HMPT,RT, 30 min; 2.) HMPT, RT, overnight

7: 1.) Li, NH₃ / 1.) THF, -78 deg C, 7 min; 2.) THF, -78 deg C, 1 min.

8: 1.) LDA / 1.) THF, 0 to 10 deg C, 20 min; 2.) THF, -78 deg C, then RT, overnight

9: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C 2.) MeOH, RT, 20 h

10: 93 percent / 1N H₂SO₄ / tetrahydrofuran / 48 h / 60 °C / aq. KOH, MeOH, THF

11: 86 percent / MgSO₄ / MeSO₃H / benzene / 24 h / Ambient temperature

12: O₃ / CH₂Cl₂ / -78 °C / 1.) -78 deg C

13: i-PrNH₂ / CH₂Cl₂ / 2 h / Ambient temperature

14: 96 percent / CH₂Cl₂ / 48 h / Ambient temperature

With borax; copper(l) iodide; aluminium trichloride; thionyl chloride; dimethylsulfide; sulfuric acid; ammonia; lithium; sodium hydride; magnesium sulfate; ozone; isopropylamine; lithium diisopropyl amide; methanesulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)87670-5

Reference yield:

(1'r,2'RS,5'SR)-1',2',5'-trimethylcyclopentylpropyn-1-one (88907-89-5) → isoptychanolide (81674-82-0,89015-22-5,108646-50-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 76 percent / 6 h / 620 °C / 14 Torr

2: 1.) CuI / 1.) diethylether, -30 deg C, 15 min; 2.) diethylether, -30 to 0 deg C, 3 h, 3.) diethylether, -60 deg C, 90 min.

3: diethyl ether

4: 1.) NaH / 1.) HMPT,RT, 30 min; 2.) HMPT, RT, overnight

5: 1.) Li, NH₃ / 1.) THF, -78 deg C, 7 min; 2.) THF, -78 deg C, 1 min.

6: 1.) LDA / 1.) THF, 0 to 10 deg C, 20 min; 2.) THF, -78 deg C, then RT, overnight

7: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C 2.) MeOH, RT, 20 h

8: 93 percent / 1N H₂SO₄ / tetrahydrofuran / 48 h / 60 °C / aq. KOH, MeOH, THF

9: 86 percent / MgSO₄ / MeSO₃H / benzene / 24 h / Ambient temperature

10: O₃ / CH₂Cl₂ / -78 °C / 1.) -78 deg C

11: i-PrNH₂ / CH₂Cl₂ / 2 h / Ambient temperature

12: 96 percent / CH₂Cl₂ / 48 h / Ambient temperature

With copper(l) iodide; dimethylsulfide; sulfuric acid; ammonia; lithium; sodium hydride; magnesium sulfate; ozone; isopropylamine; lithium diisopropyl amide; methanesulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)87670-5

upstream raw materials:

(1RS,2RS,3RS,5RS,6SR)-1,2,5,6-tetramethylbicyclo<3.3.0>octane-3-spiro-5'-2'-oxacyclopent-3'-en-1'-one

(1r,2RS,5SR)-trimethylcyclopentane-1-carboxylic acid

(1'r,2'RS,5'SR)-1',2',5'-trimethylcyclopentylpropyn-1-one

(1RS,5RS,8SR)-1,5,8-trimethylbicyclo<3.3.0>oct-3-en-2-one

Refernces

SYNTHESIS OF A STEREOISOMER OF PTYCHANOLIDE

10.1016/S0040-4039(00)88292-1

The research focuses on the synthesis of a stereoisomer of ptychanolide, a sesquiterpenoid constituent of the Liverwort Ptychanthus striatus. The purpose of the study was to address two major challenges in the synthesis process: constructing the highly methyl-substituted bicyclo[3.3.0]octane system and elaborating the S,X-epoxy X-lactone moiety. The researchers employed an α-alkynone cyclization method, which had been successfully used in constructing carbon skeletons of other polycyclopentanoid natural products. The study concluded with the successful synthesis of a stereoisomer of ptychanolide, which was confirmed through IR, 1H-, and 13C-NMR spectral comparison with the natural (+)-1, showcasing a different chemical profile.

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