Synthesis of the tetrahydropyran fragment of bistramide D

Synthesis of the tetrahydropyran fragment of bistramide D

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 buil...

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Bibliographic Details
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
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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