title: Isocomplestatin: total synthesis and stereochemical revision.
abstract: A Pd-mediated method for preparation of the strained macrocyclic moiety of complestatins is disclosed. Through stereoselective synthesis of model macrocycles and the S atropisomer of complestatin, the stereochemical identity of the anti-HIV agent complestatin is established. Investigations described herein illustrate that the compound previously reported as isocomplestatin is the same as complestatin. Thus, the S atropisomer of complestatin is the true isocomplestatin and has not been isolated as a natural product.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Toshio
authors.initials: T
authors.lastname: Shinohara
authors.forename: Hongbo
authors.initials: H
authors.lastname: Deng
authors.forename: Marc L
authors.initials: ML
authors.lastname: Snapper
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
mesh_terms: D002733:Chlorophenols / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009842:Oligopeptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D002733:Chlorophenols; D009842:Oligopeptides; D010456:Peptides, Cyclic; C023490:complestatin