Synthesis of the tetrahydropyran fragment of bistramide D
Bates, Roderick W.
Loh, Joanna Kejun
Date of Issue2014
School of Physical and Mathematical Sciences
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.
Asian journal of organic chemistry
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