Premium
Synthesis of the Tetrahydropyran Fragment of Bistramide D
Author(s) -
Bates Roderick W.,
Li Lu,
Palani Kalpana,
Phetsang Wanida,
Loh Joanna Kejun
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402052
Subject(s) - chemistry , tetrahydropyran , moiety , alkene , substituent , metathesis , intramolecular force , sulfone , isomerization , salt metathesis reaction , selectivity , stereochemistry , ring (chemistry) , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , polymer , polymerization
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.