On the total synthesis of (S)-methanophenazine and the formal synthesis of (R)-methanophenazine from a common precursor
β Scribed by Uwe Beifuss; Mario Tietze
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 79 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Methanophenazine is a new cofactor from methanogenic archaea. (S)-Methanophenazine has been synthesized from three building blocks, i.e. 2-hydroxy-phenazine, ethyl (R)-3-methylglutarate and (E,E)farnesyl acetone; a stereodivergent approach from ethyl (R)-3-methylglutarate warrants the formal synthesis of (R)-methanophenazine.
π SIMILAR VOLUMES
The formal total synthesis of epothilone A is described. The 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reactio
Scheme 2. Reagents and conditions: (a) p-TsCl, pyridine, dry CH 2 Cl 2 , 0Β°C-rt, 14 h; (b) LiAlH 4 , dry THF, 0Β°C-rt, 18 h; (c) NaH, PMBBr, dry THF, 0Β°C-rt, 4 h; (d) 60% aq. AcOH, cat. HCl, rt, 14 h; (e) NaIO 4 , MeOH/H 2 O (2:1), rt, 2 h; (f) Ph 3 P CHCOO(CH 2 ) 2 SO 2 Tol, 110Β°C, 1 h; (g) cat. HCl