Technology Process of (-)-nicolaioidesin C
There total 8 articles about (-)-nicolaioidesin C 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:
- Guidance literature:
-
C18H16O5;
With
borane-THF; (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; acetic acid;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
Molecular sieve;
Inert atmosphere;
7-methyl-3-methene-1,6-octadiene;
In
tetrahydrofuran;
at 20 ℃;
for 16h;
Molecular sieve;
Inert atmosphere;
With
sodium hydrogencarbonate;
In
methanol;
at 20 ℃;
for 4h;
enantioselective reaction;
Inert atmosphere;
DOI:10.1021/acs.joc.5b02248
- Guidance literature:
-
With
toluene-4-sulfonic acid;
In
methanol; dichloromethane;
at 40 ℃;
for 8h;
DOI:10.1002/ejoc.201800262
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 2 h / -40 °C / Inert atmosphere
1.2: 18 h / 20 °C / Inert atmosphere
2.1: dimethylaluminum chloride / hexane; dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
3.1: lithium borohydride / tetrahydrofuran; methanol; diethyl ether / 6 h / 20 °C / Inert atmosphere
4.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
5.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
5.2: 16 h / -78 - 20 °C / Inert atmosphere
6.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
7.1: toluene-4-sulfonic acid / dichloromethane; methanol / 8 h / 40 °C
With
lithium borohydride; n-butyllithium; dimethylaluminum chloride; pivaloyl chloride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1002/ejoc.201800262
