A novel strategy towards the total synthesis of cyclopeptide alkaloids

Cyclic peptides I (R = benzyl, allyl; R1 = NO2, NH2, H), which contain the macrocyclic aryl ether skeleton of some naturally occurring alkaloids such as pandamine, were prepd. Key to the synthetic strategy was the cyclocondensation of the linear peptides II [NR2 = NHBOC, N(benzyl)2, N(allyl)2; R2 = SiMe2CMe3, H] to form macrocycles I. Thus, II [NR2 = N(allyl)2, R2 = H] in a DMF soln. was treated with Bu4N+F- in the presence of mol. sieves to form I (R = allyl, R1 = NO2), which was subsequently converted first to the amine I (R = allyl, R1 = NH2) and then to the target macrocycle I (R = allyl, R1 = H). [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 35, 21, 2517-2519
Year:
1996
Keywords:
Note:
CAN 126:89619
31-6
Alkaloids
Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
0570-0833
written in English.
10233-81-5P Role: PNU (Preparation, unclassified), PREP (Preparation) (strategy toward the total synthesis of cyclopeptide alkaloids by formation of macrocyclic aryl ethers); 13734-34-4 (N-tert-Butoxycarbonyl-Phenylalanine); 90181-25-2; 185393-96-8 Role: RCT (Reactant), RACT (Reactant or reagent) (strategy toward the total synthesis of cyclopeptide alkaloids by formation of macrocyclic aryl ethers); 185393-97-9P; 185393-98-0P; 185393-99-1P; 185394-01-8P; 185394-02-9P; 185394-03-0P; 185394-04-1P; 185394-05-2P; 185394-06-3P; 185418-75-1P; 185529-05-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (strategy toward the total synthesis of cyclopeptide alkaloids by formation of macrocyclic aryl ethers); 185393-94-6P; 185393-95-7P; 185394-00-7P Role: SPN (Synthetic preparation), PREP (Preparation) (strategy toward the total synthesis of cyclopeptide alkaloids by formation of macrocyclic aryl ethers)
Laboratories:




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


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