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Synthesis of ( E )‐4‐Bromo‐3‐methoxybut‐3‐en‐2‐one, the Key Fragment in the Polyhydroxylated Chain Common to Oscillariolide and Phormidolides A–C
Author(s) -
Gil Alejandro,
LamarianoMerketegi Janire,
Lorente Adriana,
Albericio Fernando,
Álvarez Mercedes
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600770
Subject(s) - polyol , moiety , stereoselectivity , stereochemistry , chemistry , fragment (logic) , chain (unit) , organic chemistry , computer science , catalysis , algorithm , physics , polyurethane , astronomy
Abstract The terminal bromomethoxydiene (BMD) moiety of the polyhydroxylated chain present in phormidolides and oscillariolides has been synthesized for first time. Several strategies for the stereoselective synthesis of the 4‐bromo‐3‐methoxybut‐3‐en‐2‐ones are described. Furthermore, a preliminary study to successfully introduce the BMD within the polyol chain and the fatty acid allowed us to corroborate the end structure of the polyol.