Isocomplestatin: total synthesis and stereochemical revision.
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.
Shinohara
Toshio
T
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Deng
Hongbo
H
Snapper
Marc L
ML
Hoveyda
Amir H
AH
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
D002733:Chlorophenols; D009842:Oligopeptides; D010456:Peptides, Cyclic; C023490:complestatin