Technology Process of Spiro[azuleno[4,5-b]furan-9(2H),3'-[3H]benz[1,8]- azuleno[4,5-b]furan]-2,2',8,9'(1'H,3H,4'H)- tetrone,3a,4,5,5',5'a,6,6',6a,7,7',7'a,8',9a,9b,- 10'a,10'b-hexadecahydro-5'a-hydroxy-1',3,6,- 8'-tetrakis(methylene)-
There total 1 articles about Spiro[azuleno[4,5-b]furan-9(2H),3'-[3H]benz[1,8]- azuleno[4,5-b]furan]-2,2',8,9'(1'H,3H,4'H)- tetrone,3a,4,5,5',5'a,6,6',6a,7,7',7'a,8',9a,9b,- 10'a,10'b-hexadecahydro-5'a-hydroxy-1',3,6,- 8'-tetrakis(methylene)- which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 16 steps
1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / -20 - 0 °C
2.1: aluminum isopropoxide / toluene / 5 h / 140 °C / Sealed tube
3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C
4.1: copper(l) cyanide / tetrahydrofuran / 0 °C
4.2: 2 h / -78 °C
5.1: boron trifluoride diethyl etherate / chloroform; diethyl ether / 0 °C
5.2: 1.5 h / 0 - 30 °C
6.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
7.2: 2 h / -55 °C
8.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.67 h / 0 °C
9.1: dihydrogen peroxide / tetrahydrofuran; water / 0 - 25 °C
10.1: lithium diisopropyl amide / tetrahydrofuran / 0.83 h / -78 °C / Inert atmosphere
10.2: 2 h / -78 - -40 °C / Inert atmosphere
10.3: 1.5 h / 0 °C
11.1: triethylamine / dichloromethane / 0.33 h / 0 °C
12.1: neat (no solvent) / 10 h / 60 °C / Inert atmosphere
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C
14.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C
15.1: pyridinium chlorochromate / dichloromethane / 1 h / 0 °C
16.1: dicyclohexyl-carbodiimide; copper(l) chloride / dichloromethane / 4 h / 80 °C / Sealed tube
With
2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; copper(l) cyanide; aluminum isopropoxide; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; pyridinium chlorochromate; copper(l) chloride; lithium hexamethyldisilazane; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; toluene;
4.2: |Michael Addition / 12.1: |Diels-Alder Cycloaddition;
DOI:10.1002/chem.201204292