Przewaquinone E

Base Information

• Chemical Name: Przewaquinone E
• CAS No.: 96894-91-6
• Molecular Formula: C₁₈H₁₆O₅
• Molecular Weight: 312.322
• Mol file: 96894-91-6.mol

Synonyms:

Chemical Property of Przewaquinone E

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Przewaquinone E

There total 9 articles about Przewaquinone E 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:

1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione (77769-21-2) → (+)-(3R,4S)-tanshindiol B (96894-91-6,96839-30-4,97465-71-9) + tanshindiol B (97465-70-8,96839-30-4,97465-71-9)

Guidance literature:

With AD-mix β; In water; tert-butyl alcohol; at 20 ℃; for 10h; Overall yield = 77 %; Overall yield = 69 mg;

DOI:10.1039/c8ob00567b

Reference yield:

cyclohexenone (930-68-7) → (+)-(3R,4S)-tanshindiol B (96894-91-6,96839-30-4,97465-71-9) + tanshindiol B (97465-70-8,96839-30-4,97465-71-9)

Guidance literature:

Multi-step reaction with 6 steps

1: iodine; potassium carbonate; dmap / tetrahydrofuran; water / 1 h / 20 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide / tetrahydrofuran / 7 h / -78 - 20 °C

3: diethyl ether / 0.5 h / 0 °C

4: methanol / 2 h / 45 °C / Inert atmosphere; Sonication

5: toluene-4-sulfonic acid / methanol / 1 h / 80 °C

6: AD-mix-α / water; tert-butyl alcohol / 10 h / 20 °C

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; AD-mix-α; iodine; potassium carbonate; toluene-4-sulfonic acid; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether; water; tert-butyl alcohol; 2: |Negishi Coupling / 3: |Grignard Reaction / 6: |Sharpless Dihydroxylation;

DOI:10.1039/c8ob00567b

Reference yield:

2-iodocyclohex-2-en-1-one (33948-36-6) → (+)-(3R,4S)-tanshindiol B (96894-91-6,96839-30-4,97465-71-9) + tanshindiol B (97465-70-8,96839-30-4,97465-71-9)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide / tetrahydrofuran / 7 h / -78 - 20 °C

2: diethyl ether / 0.5 h / 0 °C

3: methanol / 2 h / 45 °C / Inert atmosphere; Sonication

4: toluene-4-sulfonic acid / methanol / 1 h / 80 °C

5: AD-mix-α / water; tert-butyl alcohol / 10 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; AD-mix-α; toluene-4-sulfonic acid; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether; water; tert-butyl alcohol; 1: |Negishi Coupling / 2: |Grignard Reaction / 5: |Sharpless Dihydroxylation;

DOI:10.1039/c8ob00567b

upstream raw materials:

4,5-dihydro-3-methylbenzo[1,2-b]furan-4,5-dione

(-)-(5R,6S)-5,6-dihydroxy-6-methyl-1-vinylcyclohexene 5,6-acetonide

cyclohexenone

2-iodocyclohex-2-en-1-one

Refernces

• 1、 Haiza, Mohammed,Lee, Junning,Snyder, John K.. "Asymmetric Syntheses of Salvia miltiorrhiza Abietanoid o-Quinones: Methyl Tanshinonate, Tanshinone IIB, Tanshindiol B, and 3-Hydroxytanshinone". . p. 5008 - 5013. Retrieved 2007/10/02.