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Synthesis of the C1–C13 Fragment of Kendomycin: Atropisomerism around a C−Aryl Glycosidic Bond
Author(s) -
Martin Harry J.,
Drescher Martina,
Kählig Hanspeter,
Schneider Sabine,
Mulzer Johann
Publication year - 2001
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 - 10.1002/1521-3773(20010903)40:17<3186::aid-anie3186>3.0.co;2-w
Subject(s) - atropisomer , chemistry , glycosidic bond , aryl , stereochemistry , enone , aldol reaction , fragment (logic) , organic chemistry , catalysis , alkyl , computer science , programming language , enzyme
The left‐hand fragment 2 of the novel antibiotic kendomycin ( 1 ) has been synthesized by an aldol addition and a Michael‐type 1,4‐addition of a C5 alcohol with a C9–C11 enone. Compound 2 shows an interesting atropisomerism around the C4a‐C5‐sp 2 ‐sp 3 bond. The atropisomers can be separated in pure forms by low‐temperature high‐pressure liquid chromatography.