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Linear Total Synthesis of (–)‐ACRL Toxin III B
Author(s) -
Mulzer Johann,
Dupré Susanne,
Buschmann Jürgen,
Luger Peter
Publication year - 1993
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.199314521
Subject(s) - aldol reaction , carbanion , propionate , aldehyde , chemistry , ether , stereochemistry , sequence (biology) , toxin , organic chemistry , biochemistry , catalysis
Enantio‐ and diastereomerically pure samples of the methyl ether 1 of ACRL toxin IIIA can be prepared in 16 or 20 steps from methyl 3‐hydroxy‐2‐methylpropionate. As an alternative to the aldol method the anti ‐configurated propionate units are stereoselectively produced by carbanion‐aldehyde addition with a subsequent oxidation–reduction sequence.