Intramolecular aminolysis of trichloroethyl esters: a mild macrocyclization protocol for the preparation of cryptophycin derivatives

Tetrahedron: Asymmetry
1998.0

Abstract

The bifunctional catalyst 2-hydroxypyridine (2-pyridone) is shown to promote the intramolecular aminolysis of the polyfunctionalized long-chain amino trichloroethyl ester 8 to afford cryptophycin-51 (4). This process for the construction of the macrocyclic core of cryptophycin derivatives is noteworthy for its convenience, avoidance of expensive coupling reagents, and use of mild reaction conditions. © 1998 Elsevier Science Ltd. All rights reserved.

Knowledge Graph

Similar Paper

Intramolecular aminolysis of trichloroethyl esters: a mild macrocyclization protocol for the preparation of cryptophycin derivatives
Tetrahedron: Asymmetry 1998.0
A Convergent Approach to Cryptophycin 52 Analogues:  Synthesis and Biological Evaluation of a Novel Series of Fragment A Epoxides and Chlorohydrins
Journal of Medicinal Chemistry 2003.0
An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating
Molecules 2022.0
Synthesis and biological evaluation of novel cryptophycin analogs with modification in the β-alanine region
Bioorganic & Medicinal Chemistry Letters 1999.0
Pyrrolizidine alkaloid analogues. Synthesis of macrocyclic diesters of (±)-synthanecine A from (±)-3-chloromethyl-2-hydroxymethyl-1-methyl-2,5-dihydropyrrolium chloride
J. Chem. Soc., Perkin Trans. 1 2004.0
Cryptophycin affinity labels: synthesis and biological activity of a benzophenone analogue of cryptophycin-24
Bioorganic & Medicinal Chemistry Letters 2003.0
Intramolecular (4+3) Cycloadditions of Oxidopyridinium Ions: Towards Daphnicyclidin A
Chemistry – A European Journal 2022.0
Halohydrin analogues of cryptophycin 1: Synthesis and biological activity
Bioorganic & Medicinal Chemistry Letters 1998.0
A New Trimeric Cinchona Alkaloid as a Chiral Phase-Transfer Catalyst for the Synthesis of Asymmetric α-Amino Acids
Synthesis 2005.0
Structure determination, conformational analysis, chemical stability studies, and antitumor evaluation of the cryptophycins. Isolation of 18 new analogs from Nostoc sp. strain GSV 224
Journal of the American Chemical Society 1995.0