Dodecahydro-4,8-dihydroxy-3,6,9-tris(methylene)azuleno[4,5-b]furan-2-one

Base Information

• Chemical Name: Dodecahydro-4,8-dihydroxy-3,6,9-tris(methylene)azuleno[4,5-b]furan-2-one
• CAS No.: 35730-79-1
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306
• Mol file: 35730-79-1.mol

Synonyms:Dodecahydro-4,8-dihydroxy-3,6,9-tris(methylene)azuleno[4,5-b]furan-2-one

Chemical Property of Dodecahydro-4,8-dihydroxy-3,6,9-tris(methylene)azuleno[4,5-b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dodecahydro-4,8-dihydroxy-3,6,9-tris(methylene)azuleno[4,5-b]furan-2-one

There total 42 articles about Dodecahydro-4,8-dihydroxy-3,6,9-tris(methylene)azuleno[4,5-b]furan-2-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: 75.0%

(3aR,4S,6aR,8S,9aR,9bR)-8-((tert-butyldimethylsilyl)oxy)-4-hydroxy-3,6,9-trimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one → deacylcynaropicrin (35932-46-8,89647-87-0,31565-50-1,35730-79-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.bmcl.2019.04.004

Reference yield: 70.0%

C27H46O4Si2 → (±)-integrifolin (35730-79-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201601275

Reference yield: 68.0%

(1R,3S,5R,6R,7R,8S)-8-hydroxy-3-(methoxymethoxy)-13,14,15-trimethylenedecahydroazuleno[6,7-β]furan-12-one (1549718-88-8) → deacylcynaropicrin (35932-46-8,89647-87-0,31565-50-1,35730-79-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In tert-butyl alcohol; for 28h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmcl.2013.12.099

upstream raw materials:

8-epideacylcynaropicrin-3-O-β-D-glucopyranoside

ixerin M

ixerin N

ixerin R

Downstream raw materials:

8α-acetoxyzaluzanin D

Refernces

• 1、 Shimomaki, Katsuya,Kusama, Hiroyuki,Iwasawa, Nobuharu. "Total Synthesis of (±)-Integrifolin". . p. 9953 - 9957. Retrieved 2016/07/19.
• 2、 Macías, Francisco A.,Vi?olo, Victor M.I.,Fronczek, Frank R.,Massanet, Guillermo M.,Molinillo, José M.G.. "11,16 Oxetane lactones. Spectroscopic evidences and conformational analysis". . p. 7747 - 7755. Retrieved 2007/10/03.