Premium
An Expeditious Asymmetric Synthesis of Polyfunctional 1,7‐Dioxaspiro[5.5]undecanes
Author(s) -
GerberLemaire Sandrine,
Vogel Pierre
Publication year - 2004
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.200400514
Subject(s) - chemistry , stereoselectivity , butane , diol , stereochemistry , surface modification , enantioselective synthesis , organic chemistry , catalysis
Quick access to polyfunctional spiroketal (3 R )‐4[(2 S ,6 R ,8 R ,10 S )‐4,4‐bis(ethylthio)‐10‐hydroxy‐8‐(2‐hydroxyethyl)‐1,7‐dioxaspiro[5.5]undec‐2‐yl]butane‐1,3‐diol [(+)‐ 19 ] is now available through the stereoselective functionalization of enantiomerically pure protected tetrol (4 R ,4′ R ,6 R ,6′ R )1,1′‐methylenebis[4‐[(benzyloxy)methoxy]‐6‐[(triethylsilyl)oxy]cyclohept‐1‐ene [(−)‐ 9 ], derived from 2,2′‐methylenedifuran. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)