Total synthesis of putative montamine and a proposed structural reassignment

The natural product montamine was originally assigned as a homodimer of moschamine linked by a N-N' bond at the serotonin side-chain. A total synthesis of the reported structure has shown this to be incorrect. Analysis of the spectroscopic data suggests that the dimerization site has been incor...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-09, Vol.12 (35), p.6878-6884
Main Authors: Blair, Lachlan M, Colby Davie, Elizabeth A, Sperry, Jonathan
Format: Article
Language:English
Subjects:
Biological Products - chemistry
Chemistry, Pharmaceutical - methods
Coumaric Acids - chemical synthesis
Dimerization
Drug Design
Ethers - chemistry
Indole Alkaloids - chemical synthesis
Magnetic Resonance Spectroscopy
Molecular Structure
Protons
Serotonin - chemistry
Spectrophotometry - methods
Stereoisomerism
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Summary:The natural product montamine was originally assigned as a homodimer of moschamine linked by a N-N' bond at the serotonin side-chain. A total synthesis of the reported structure has shown this to be incorrect. Analysis of the spectroscopic data suggests that the dimerization site has been incorrectly assigned, and montamine is likely to be a 4,4'-bismoschamine natural product previously described in the literature.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01304b