(+)-deoxyvernolepin

Base Information

• Chemical Name: (+)-deoxyvernolepin
• CAS No.: 60872-71-1
• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.29
• Mol file: 60872-71-1.mol

Synonyms:

Chemical Property of (+)-deoxyvernolepin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-deoxyvernolepin

There total 17 articles about (+)-deoxyvernolepin 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: 82.0%

(3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione (76338-18-6,76375-88-7) → (+)-deoxyvernolepin (59076-96-9,60872-71-1)

Guidance literature:

With dihydrogen peroxide;

DOI:10.1016/S0040-4039(00)78702-8

Reference yield: 62.0%

(3R,5aR,9S,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione (76338-18-6,76375-88-7) → (+)-deoxyvernolepin (59076-96-9,60872-71-1) + (5aR,9bS)-9-Methyl-3-methylene-5a-vinyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione (76338-19-7)

Guidance literature:

With dihydrogen peroxide;

DOI:10.1016/S0040-4039(00)78702-8

Reference yield:

tetrahydrosantonin (13902-54-0,13902-55-1,13902-61-9,14794-68-4,14804-46-7,14804-47-8,14987-66-7,17956-11-5,18409-87-5,32638-47-4,84652-34-6,143521-75-9,143521-76-0) → (+)-deoxyvernolepin (59076-96-9,60872-71-1)

Guidance literature:

Multi-step reaction with 14 steps

1: boron trifluoride etherate

2: tetramethylammonium acetate / various solvent(s) / 8 h / Heating

3: 100 percent / sodium borohydride / methanol; CH₂Cl₂ / 0.5 h / -15 - -10 °C

4: 78.5 percent / HgO, I₂ / benzene / 3 h / Heating

5: KOH / methanol

6: pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

7: 26 percent / Zn / ZnI₂ or ZnCl₂ / acetic acid / Heating

8: pyridinium p-toluenesulfonate / methanol / 3 h / Heating

9: 1) O₃, CH₃OH + CH₂Cl₂, -78 deg C, 2) NaBH₄, -20 deg C

10: 72 percent / 10 percent HCl / methanol / Heating

11: (C₄H₉)3P

12: H₂O₂

13: 1) LDA, -78 deg C, THF, 2) -40 deg C, THF - HMPA

14: 25 percent / H₂O₂

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; (C₄H₉)3P; tetramethyl ammonium acetate; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; pyridinium chlorochromate; mercury(II) oxide; zinc; boron trifluoride diethyl etherate; zinc(II) iodide; zinc(II) chloride; In methanol; dichloromethane; acetic acid; benzene;

DOI:10.1016/S0040-4039(00)78702-8

upstream raw materials:

(3R,5aR,9S,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione

(3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione

tetrahydrosantonin

C₁₅H₂₂O₄