A new access to 14-membered macrocycle: synthesis of model F-O-G ring of teicoplanin

A new strategy based upon the intramol. SNAr reaction was developed for the synthesis of I, the 14-membered F-O-G macrocyclic ring system of teicoplanin. Thus, treatment of acyclic precursor II (X = F) with CsF or K2CO3/18-crown-6 in DMF at room temp. for 6-20 h gave 62-82% I. Chloride II (R = Cl) gave 80% I on treatment with K2CO3 in DMF at 80 Deg for 6 h. The reason for the easy macrocyclization was advanced and supported by computational studies. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 36, 8, 1279-82
Year:
1995
Keywords:
Note:
CAN 122:315079
34-3
Amino Acids, Peptides, and Proteins
Inst. Chim. Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0040-4039
written in English.
61036-62-2P (Teicoplanin) Role: PNU (Preparation, unclassified), PREP (Preparation) (prepn. of 14-membered teicoplanin F-O-G ring system model macrocycle by intramol. nucleophilic arom. substitution); 873-62-1 (3-Hydroxybenzonitrile); 4530-20-5 (N-tert-Butoxycarbonylglycine); 163395-24-2; 163395-25-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of 14-membered teicoplanin F-O-G ring system model macrocycle by intramol. nucleophilic arom. substitution); 13269-15-3P; 147949-76-6P; 163395-22-0P; 163395-23-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 14-membered teicoplanin F-O-G ring system model macrocycle by intramol. nucleophilic arom. substitution); 163395-21-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of 14-membered teicoplanin F-O-G ring system model macrocycle by intramol. nucleophilic arom. substitution)
Laboratories:




 Record created 2010-11-25, last modified 2018-09-13


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)