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Towards the Synthesis of the 4,19‐Diol Derivative of (–)‐Mycothiazole: Synthesis of a Potential Key Intermediate
Author(s) -
Batt Frédéric,
Fache Fabienne
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100669
Subject(s) - chemistry , derivative (finance) , metathesis , diol , halogen , nucleophile , iodide , total synthesis , combinatorial chemistry , enantioselective synthesis , sodium iodide , salt metathesis reaction , stereochemistry , organic chemistry , catalysis , alkyl , financial economics , economics , polymerization , polymer
The synthesis of a potential key intermediate for the synthesis of the 4,19‐diol derivative of (–)‐mycothiazole using convergent strategies is described in this paper. Several approaches have been tested, including cross metathesis and a Julia–Kocienski olefination. Finally, the formation of the 1,1‐dialkyl‐1,2‐ethanediol motif through C4–C5 bond construction was realized by nucleophilic addition of a vinyl iodide derivative to a keto ester after halogen/lithium exchange followed by reduction of the resulting hydroxy ester.