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Total Synthesis of an Atropdiastereomer of RP‐66453 and Determination of Its Absolute Configuration
Author(s) -
BoisChoussy Michèle,
Cristau Pierre,
Zhu Jieping
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351996
Subject(s) - intramolecular force , absolute configuration , chemistry , nucleophilic aromatic substitution , natural product , total synthesis , sequence (biology) , stereochemistry , absolute (philosophy) , computer science , nucleophilic substitution , organic chemistry , philosophy , theology , biochemistry
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 S N Ar‐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.