- Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: Synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8′-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents
-
An improved sulfenylation method for the preparation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines from diketopiperazines has been developed. Employing NaHMDS and related bases and elemental sulfur or bis[bis(trimethylsilyl)amino]trisulfide (23) in THF, the developed method was applied to the synthesis of a series of natural and designed molecules, including epicoccin G (1), 8,8′-epi-ent-rostratin B (2), gliotoxin (3), gliotoxin G (4), emethallicin E (5), and haematocin (6). Biological screening of selected synthesized compounds led to the discovery of a number of nanomolar antipoliovirus agents (i.e., 46, 2,2′-epi-46, and 61) and several low-micromolar anti-Plasmodium falciparum lead compounds (i.e., 46, 2,2′-epi-46, 58, 61, and 1).
- Nicolaou, K. C.,Lu, Min,Totokotsopoulos, Sotirios,Heretsch, Philipp,Giguere, Denis,Sun, Ya-Ping,Sarlah, David,Nguyen, Thu H.,Wolf, Ian C.,Smee, Donald F.,Day, Craig W.,Bopp, Selina,Winzeler, Elizabeth A.
-
supporting information
p. 17320 - 17332,13
(2020/09/02)
-
- A practical sulfenylation of 2,5-diketopiperazines
-
Sulfurs in action: A practical and simple method has been developed for the introduction of sulfur atoms into 2,5-diketopiperazines (I) under mild conditions. The reaction provides more or less complex epidithiodiketopiperazines (II) and bis-methylthiodik
- Nicolaou,Giguere, Denis,Totokotsopoulos, Sotirios,Sun, Ya-Ping
-
supporting information; experimental part
p. 728 - 732
(2012/03/08)
-
- TOTAL SYNTHESIS OF GLIOTOXIN, DEHYDROGLIOTOXIN AND HYALODENDRIN
-
Two general methods, Method A and Method B in Scheme 19, to synthesize epidithiapiperazinediones, are described.A total synthesis of racemic and optically active gliotoxin (1) and of racemic dehydrogliotoxin (53) was achieved by using Method A, whereas a total synthesis of racemic hyalodendrin (52) was completed by using Method B.
- Fukuyama, Tohru,Nakatsuka, Shin-Ichi,Kishi, Yoshito
-
p. 2045 - 2078
(2007/10/02)
-