Total Synthesis of an Atropdiastereomer of RP-66453 and Determination of Its Absolute Configuration

The absolute configuration (aR, S, S, S, S, S) was assigned to the natural product RP‐66453 (1) after the total synthesis of its atropdiastereomer and spectroscopic studies on the two compounds. A sequence of SNAr‐based cycloetherification and an intramolecular atropdiastereoselective Suzuki–Miyaura...

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Published in:Angewandte Chemie International Edition 2003-09, Vol.42 (35), p.4238-4241
Main Authors: Bois-Choussy, Michèle, Cristau, Pierre, Zhu, Jieping
Format: Article
Language:English
Subjects:
atropisomerism
Biological Factors - chemical synthesis
macrocycles
Magnetic Resonance Spectroscopy
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Stereoisomerism
structure elucidation
Suzuki-Miyaura reaction
Thermodynamics
total synthesis
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description The absolute configuration (aR, S, S, S, S, S) was assigned to the natural product RP‐66453 (1) after the total synthesis of its atropdiastereomer and spectroscopic studies on the two compounds. A sequence of SNAr‐based cycloetherification and an intramolecular atropdiastereoselective Suzuki–Miyaura coupling were used for the construction of the elusive A‐B‐O‐C bicyclic skeleton of RP‐66453.
doi_str_mv 10.1002/anie.200351996
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subjects atropisomerism
Biological Factors - chemical synthesis
macrocycles
Magnetic Resonance Spectroscopy
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Stereoisomerism
structure elucidation
Suzuki-Miyaura reaction
Thermodynamics
total synthesis
title Total Synthesis of an Atropdiastereomer of RP-66453 and Determination of Its Absolute Configuration
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