Premium
Relative and Absolute Configuration of Filipin III
Author(s) -
Rychnovsky Scott D.,
Richardson Timothy I.
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199512271
Subject(s) - filipin , stereocenter , absolute configuration , chemistry , absolute (philosophy) , sequence (biology) , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , enantioselective synthesis , biochemistry , philosophy , epistemology , membrane , catalysis
NMR spectroscopy, Mosher's ester analysis, degradation , and synthesis of the C26–C27 fragment unraveled the relative and absolute configuration of the natural antibiotic, filipin III. The relative configurations for the nine stereogenic centers in the top half of the formula for filipin shown on the right were determined from just three acetonide derivatives that arose in a two‐step protection sequence.