Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals

• Main Authors: Liao, Hongze, Leng, Wei-Lin, Hoang, Kim Le Mai, Yao, Hui, He, Jingxi, Voo, Amanda Ying Hui, Liu, Xue-Wei
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2017
• Subjects: Asymmetric Synthesis; Glycals
• Online Access: https://hdl.handle.net/10356/86867; http://hdl.handle.net/10220/44230
• Institution: Nanyang Technological University

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 cy...