Synthesis and bioactivity of (±)-tetrahydrohaliclonacyclamine A

The total synthesis of tetrahydrohaliclonacyclamine A ( 5) is described. A key step involves the hydrogenation of an unsaturated bis-piperidine incorporated into a 17-membered macrocycle to provide the cis–syn–cis stereochemistry common to haliclonacyclamines A–D. The hydrogenation product is advanc...

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Bibliographic Details
Published in:Tetrahedron 2010-06, Vol.66 (26), p.4805-4810
Main Authors: Smith, Brian J., Qu, Tao, Mulder, Matthew, Noetzel, Meredith J., Lindsley, Craig W., Sulikowski, Gary A.
Format: Article
Language:English
Subjects:
Marine alkaloid
Muscarinic M1 antagonist
Ring-closing metathesis
Stereoselective hydrogenation
Stille cross-coupling
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Summary:The total synthesis of tetrahydrohaliclonacyclamine A ( 5) is described. A key step involves the hydrogenation of an unsaturated bis-piperidine incorporated into a 17-membered macrocycle to provide the cis–syn–cis stereochemistry common to haliclonacyclamines A–D. The hydrogenation product is advanced to the title compound following a five-step reaction sequence. Tetrahydrohaliclonacyclamine A is shown to bind to a variety of ion channels/GPCRs and act as a muscarinic M 1 antagonist. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.03.117