Michèle Bois-Choussy

Synthesis of diastereomers of complestatin and chloropeptin I: substrate-dependent atropstereoselectivity of the intramolecular Suzuki-Miyaura reaction

Atropisomers as well as CC2 epimers of complestatin and chloropeptin I are readily synthesized through an intramol. SNAr reaction and the Suzuki-Miyaura reaction. The abs. configuration of amino acid N-methyl-2-(3,5-dichloro-4-hydroxyphenyl)glycine was found to det. the atropselectivity of the aryl-aryl bond-forming reaction. [on SciFinder (R)]

Total synthesis of complestatin (Chloropeptin II)

Complestatin was isolated in 1980 from the mycelium of Streptomyces lavendulae as inhibitor of alternative pathways to the complement cascade. An efficient synthesis of complestatin was developed. Intramol. Suzuki-Miyaura and SNAr reactions were employed for the construction of two macrocycles by the formation of aryl-aryl and aryl-aryl ether bonds, resp. A [3+3] segment coupling was used for the construction of the hexapeptide backbone, which makes this synthesis highly convergent. [on SciFinder (R)]

Rapid and efficient solid phase syntheses of cyclic peptides with endocyclic biaryl ether bonds

Solid phase syntheses of the OF4949 derivs. I (R = H, CH2CONH2) and II (R1 = H, R2 = H, NH2; R1 = NH2, R2 = H) were performed via protection/deprotection of tyrosine side chains on a support, and SNAr macrocyclization reactions. [on SciFinder (R)]

Palladium catalyzed reductive deprotection of alloc: Transprotection and peptide bond formation

N-allyloxycarbonyl group could be efficiently removed using sodium borohydride as hydride donor in the presence of catalytic amount of palladium (0). The conditions were applied to chemoselective protecting group transformation (transprotection) and peptide bond formation.

Recent progress in isolation, bioactivity evaluation and total synthesis of diarylheptanoids

A review with 124 refs. on the isolation, bioactivity evaluation, biosynthesis, and total synthesis of diarylheptanoids. [on SciFinder (R)]

Synthesis of a modified carboxylate-binding pocket of vancomycin

A 16-membered tetrapeptide macrocycle I, an analog of the vancomycin binding pocket, has been designed and synthesized using the efficient macrocyclization of the corresponding linear tetrapeptide via biaryl ether formation. In acetone, I adopted a right conformation needed for binding carboxylate anion even in the absence of -Ac-D-Ala-D-Ala-OH. [on SciFinder (R)]

Phenoxide and naphthoxide ions as nucleophiles for SRN1 reactions: Synthesis of biphenyl and phenylnaphthyl derivatives

Abstract Biphenyl or phenylnaphthyl derivatives are obtained by photostimulated SRN1 reactions between the anion of phenols or naphthols and variously substituted haloarenes.

Chemoenzymatic synthesis of enantiomerically pure 4-fluoro-3-nitro and 3-fluoro-4-nitro phenylalanine

Enantiomerically pure L- and D-4-fluoro-3-nitrophenylalanines and L- and D-3-fluoro-4-nitrophenylalanines were obtained from their corresponding racemates via enzymic resoln. [on SciFinder (R)]

A common and general access to berberine and benzo [c] phenanthridine alkaloids

Abstract The S RN 1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a high-yielding and versatile access to both classes of alkaloids.

Studies on SRN1 reactions. Part 8 : New and direct arylation and hetarylation of β-dicarbonyl compounds by SRN1☆

Arylation of β-dicarbonyl compounds is carried out by photostimulated SRN1 reaction between bromo-benzonitriles or bromocyanopyridine and β-dicarbonyl derived monoanions.