Journal
TETRAHEDRON
Volume 66, Issue 26, Pages 4805-4810Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.03.117
Keywords
Marine alkaloid; Ring-closing metathesis; Stereoselective hydrogenation; Stille cross-coupling; Muscarinic M1 antagonist
Categories
Funding
- National Institutes of Health [GM067726]
- Vanderbilt Institute of Chemical Biology
Ask authors/readers for more resources
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. (C) 2010 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available
Share Paper
