Synthesis of the central tryptophan-leucine residue of celogentin C

Synlett

Volumn , Issue 10, 2008, Pages 1532-1536

  Michaux, Julien ^a   Retaillea, Pascal ^a   Campagne, Jean Marc ^b  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Asymmetric catalysis; Natural products; Palladium; Rhodium; Total synthesis

Indexed keywords

CELOGENTIN C; ENAMINE; IMINE; LEUCINE; MOROIDIN; NATURAL PRODUCT; PALLADIUM; RHODIUM; STEPHANOTIC ACID; TRYPTOPHAN DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; DRUG SYNTHESIS; HECK REACTION; HYDROGENATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SUZUKI REACTION;

EID: 46449103202     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078411     Document Type: Article

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40. In examples described in the literature, asymmetric hydrogenations with (S,5)-MeBPE [or (5,5)-MeDuphos] have generally been described to give (5)-amino acids (ref. 19 and 20) as expected in the leucine part of celogentin C. In our synthesis, this diastereoselectivity outcome could not be yet confirmed; efforts to obtain a crystalline structure to confirm this diasteroselectivity were to date unsuccessful. Hopefully, we are expecting to get further information on this topic after the introduction of the left-handed peptidic part of celogentin C. By the way, in the presence of the (7?,7J)-MeBPE ligand, a 16:84 dr was obtained illustrating the role of the remote tryptophan chiral center in the asymmetric hydrogenation.