191542-08-2Relevant articles and documents
Next-Generation Total Synthesis of Vancomycin
Boger, Dale L.,Cai, Yu,Jamin Keith, D.,Mogi, Yuzo,Moore, Maxwell J.,Qu, Shiwei,Tan, Ceheng
supporting information, p. 16039 - 16050 (2020/10/02)
A next-generation total synthesis of vancomycin aglycon is detailed that was achieved in 17 steps (longest linear sequence, LLS) from the constituent amino acid subunits with kinetically controlled diastereoselective introduction of all three elements of atropisomerism. In addition to new syntheses of three of the seven amino acid subunits, highlights of the approach include a ligand-controlled atroposelective one-pot Miyaura borylation-Suzuki coupling sequence for introduction of the AB biaryl axis of chirality (>20:1 dr), an essentially instantaneous and scalable macrolactamization of the AB ring system nearly free of competitive epimerization (>30:1 dr), and two room-temperature atroposelective intramolecular SNAr cyclizations for sequential CD (8:1 dr) and DE ring closures (14:1 dr) that benefit from both preorganization by the preformed AB ring system and subtle substituent effects. Combined with a protecting group free two-step enzymatic glycosylation of vancomycin aglycon, this provides a 19-step total synthesis of vancomycin. The approach paves the way for large-scale synthetic preparation of pocket-modified vancomycin analogues that directly address the underlying mechanism of resistance to vancomycin.
Synthesis of linear tripeptides for right-hand segments of complestatin
Yamada, Yaeko,Akiba, Ai,Arima, Shiho,Okada, Chiharu,Yoshida, Kiminari,Itou, Fumihiro,Kai, Toshitsugu,Satou, Toshiko,Takeda, Kazuyoshi,Harigaya, Yoshihiro
, p. 1277 - 1290 (2007/10/03)
This paper concerns a synthetic study of the right-hand segment of complestatin, an inhibitor of gp120-CD4 receptor. The effective synthesis of four important precursors for the right-hand segment of complestatin is described. Two of them are the precurso
Complestatin synthetic studies: The effect of the amino acid configuration on peptide backbone conformation in the common western BCD macrocycle
Smith III, Amos B.,Chruma, Jason J.,Han, Qiang,Barbosa, Joseph
, p. 1697 - 1702 (2007/10/03)
The synthesis and structural analysis, involving X-ray crystallographic, nuclear magnetic resonance, and computational studies of four diastereomers of the common western BCD diarylether macrocycle of the complestatins, a family of HIV entry inhibitors, h
Synthetic studies towards the synthesis of western and eastern chloropeptin I, II subunits
Roussi, Georges,Gonzalez Zamora, Eduardo,Carbonnelle, Annie-Claude,Beugelmans, Rene
, p. 2041 - 2063 (2007/10/03)
The western subunit (16-membered ring) was synthesized by the intramolecular SNAr reaction while the first 16-membered ring compound was obtained as a model of the eastern subunit via an intramolecular Ni0 mediated coupling reaction.
Expeditious syntheses of two arylglycine derivatives corresponding to the central amino acid of the vancomycin family of antibiotics
Pearson, Anthony J.,Chelliah, Mariappan V.,Bignan, Gilles C.
, p. 536 - 540 (2007/10/03)
Two expeditious and efficient syntheses (in 7 and 4 steps, respectively) are described for the central amino acid part of the vancomycin family. The first method constitutes a concise asymmetric synthesis, starting from 4- hydroxyphenylacetic acid, of (R)-(3,5-dihydroxy-4-methoxyphenyl)glycine derivatives using Evans' asymmetric azidation methodology. In the second approach, an efficient synthesis of a protected 3,5-dichloro-4- methoxyphenylglycine derivative is described, starting from commercially available (R)-4-hydroxyphenylglycine. These two syntheses are much shorter and operationally simpler than those previously described, and are currently employed in an effort towards the construction of the bicyclic system of vancomycin and ristocetin.
Synthesis of a model of chloropeptins I, II western subunit by the intramolecular S(N)Ar based methodology
Roussi, Georges,Zamora, Eduardo Gonzalez,Carbonnelle, Annie-Claude,Beugelmans, Rene
, p. 4401 - 4404 (2007/10/03)
Formation of a biaryl ether bond between the termini of a tetrapeptide containing a highly racemization prone amino acid by the intramolecular SNAr reaction afforded two diastereomeric 16-membered macrocycles along with their respective atropoisomers. The (R,S,R) and its atropoisomer constituted model of chloropeptins I, II, western part.
