Isocomplestatin: Total Synthesis and Stereochemical Revision
- 28 April 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (20), 7334-7336
- https://doi.org/10.1021/ja051790l
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.Keywords
This publication has 16 references indexed in Scilit:
- Total Synthesis of an Atropdiastereomer of RP‐66453 and Determination of Its Absolute ConfigurationAngewandte Chemie International Edition, 2003
- Total Synthesis of Anti-HIV Agent Chloropeptin IJournal of the American Chemical Society, 2003
- Complestatin to chloropeptin I via a quantitative acid catalyzed rearrangement. Absolute stereochemical determination of complestatin.Tetrahedron Letters, 1998
- Synthesis of arylboronates via the palladium(0)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflatesTetrahedron Letters, 1997
- Stereostructure of (−)-Chloropeptin I, a Novel Inhibitor of gp120−CD4 Binding, via High- Temperature Molecular Dynamics, Monte Carlo Conformational Searching, and NMR SpectroscopyJournal of the American Chemical Society, 1996
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic EstersThe Journal of Organic Chemistry, 1995
- Iodination of phenols using chloramine T and sodium iodideTetrahedron Letters, 1985
- An improved procedure for the iodination of phenols using sodium iodide and tert-butyl hypochloriteThe Journal of Organic Chemistry, 1985
- Formation and reactions of the cyclic tautomers of tryptophans and tryptamines. VII. Hydroxylation of tryptophans and tryptamines.CHEMICAL & PHARMACEUTICAL BULLETIN, 1984