Technology Process of (+)-muricatacin
There total 3 articles about (+)-muricatacin which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
titanium(IV) isopropylate; hydrogen; (R)-1,1'-Bi-2-naphthol;
palladium on activated charcoal;
Yield given. Multistep reaction. Yields of byproduct given;
1.) CH2Cl2, -20 deg C, 1.5 h, 2.) CH2Cl2, toluene, room temp., 12 h;
DOI:10.1021/jo9804137
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 98 percent / MnO2 / hexane / 24 h / 20 °C
2: 93 percent / 18-crown-6; t-BuOK / tetrahydrofuran / 2.5 h / -78 °C
3: OsO4; MeSO2NH2; (DHQ)2PHAL / K3Fe(CN)6; K2CO3 / 2-methyl-propan-2-ol; H2O / 0 °C
4: 97 percent / H2 / Pd/C / methanol / 24 h / 760 Torr
With
manganese(IV) oxide; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; 18-crown-6 ether; methanesulfonamide; potassium tert-butylate; hydrogen;
palladium on activated charcoal; potassium carbonate; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; hexane; water; tert-butyl alcohol;
2: Still-Gennari reaction / 3: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo061057s
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -24 °C / Molecular sieve; Inert atmosphere
1.2: 4 h / -24 °C / Inert atmosphere
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / Inert atmosphere
3.1: benzene / 1 h / Reflux; Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0); boric acid / tetrahydrofuran / 0.17 h / 20 °C
5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h
6.1: toluene-4-sulfonic acid / methanol / 5 h / 20 °C
With
titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium(0); 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; L-(+)-diisopropyl tartrate; palladium 10% on activated carbon; hydrogen; boric acid; toluene-4-sulfonic acid;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; benzene;
1.1: Katsuki-sharpless assymetric epoxidation / 1.2: Katsuki-sharpless assymetric epoxidation / 3.1: Wittig olefination;
DOI:10.2174/157017812801264656