A total synthesis of (+)-negamycin through isoxazolidine allylation

• Main Authors: Bates, Roderick Wayland, Khanizeman, Rab'iah Nisha, Hirao, Hajime, Tay, Yu Shan, Sae-Lao, Patcharaporn
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2014
• Subjects: Science::Chemistry::Organic chemistry::Organic synthesis
• Online Access: https://hdl.handle.net/10356/103102; http://hdl.handle.net/10220/24385
• Institution: Nanyang Technological University

The β-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate. The key allylation reaction proceeded with complete trans-selectivity, which is attributed to electrostatic attraction between the chlorine atom a...