An easy access to functionalized diaryl ethers: formal total synthesis of K-13

As an alternative to the Ullmann ether synthesis, the SNAr reaction led to an efficient one step synthesis of chiral bis-amino acid diaryl ethers, e.g. the reaction of 2-FC6H4NO2 with tyrosine deriv. Boc-Tyr-OMe in the presence of base gave diaryl ether I. The above diaryl ethers are important intermediates in the synthesis of K-13 II. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 35, 31, 5649-52
Year:
1994
Keywords:
Note:
CAN 122:161290
34-3
Amino Acids, Peptides, and Proteins
Inst. Chimie Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0040-4039
written in English.
95-84-1; 446-33-3; 446-34-4; 1493-27-2; 4326-36-7; 56613-80-0 Role: RCT (Reactant), RACT (Reactant or reagent) (SNAr reaction for an efficient one step synthesis of diaryl ethers); 161138-95-0P; 161138-96-1P; 161138-97-2P; 161138-98-3P; 161138-99-4P; 161139-00-0P Role: SPN (Synthetic preparation), PREP (Preparation) (SNAr reaction for an efficient one step synthesis of diaryl ethers); 36394-75-9 Role: RCT (Reactant), RACT (Reactant or reagent) (conversion of tyrosine derivs. into lactamides); 108890-90-0P (K-13) Role: PNU (Preparation, unclassified), PREP (Preparation) (formal total synthesis of K-13); 2440-79-1; 160247-85-8; 161139-04-4; 161139-05-5 Role: RCT (Reactant), RACT (Reactant or reagent) (formal total synthesis of K-13 via SNAr reaction for the synthesis of diaryl ethers); 161139-06-6P; 161139-07-7P; 161139-08-8P; 161139-09-9P; 161139-10-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (formal total synthesis of K-13 via SNAr reaction for the synthesis of diaryl ethers); 161139-01-1P; 161139-02-2P; 161139-03-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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