Synthesis of the tetrahydropyran fragment of bistramide D

• Main Authors: Bates, Roderick Wayland, Li, Lu, Palani, Kalpana, Phetsang, Wanida, Loh, Joanna Kejun
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2014
• Subjects: Science::Chemistry::Organic chemistry; Bistramide D; Metathesis
• Online Access: https://hdl.handle.net/10356/101581; http://hdl.handle.net/10220/24157
• Institution: Nanyang Technological University

A synthesis of the tetrahydropyran (THP) moiety of bistramide D has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions.