Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[126.96.36.199]undecane from glycals
Hoang, Kim Le Mai
Voo, Amanda Ying Hui
Date of Issue2017
School of Physical and Mathematical Sciences
Herein, we describe an efficient method to prepare enantiomerically pure 8-oxabicyclo[3.2.1]octanes via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement of glycal derived 1,6-enyne bearing propargylic carboxylates. The resultant compounds could then undergo interrupted Nazarov cyclization to afford diastereomerically pure 11-oxatricyclo[188.8.131.52]undecanes.
© 2017 The Author(s) (published by Royal Society of Chemistry). This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.