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An Expeditious Asymmetric Synthesis of Polyfunctional 1,7-Dioxaspiro[5.5]undecanes

✍ Scribed by Sandrine Gerber-Lemaire; Pierre Vogel

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
178 KB
Volume
2004
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

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)

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