title: Total synthesis of putative montamine and a proposed structural reassignment.
abstract: 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.
authors: School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand. j.sperry@auckland.ac.nz.
authors: Lachlan M
authors: LM
authors: Blair
authors: Elizabeth A
authors: EA
authors: Colby Davie
authors: Jonathan
authors: J
authors: Sperry
mesh_terms: D001688:Biological Products / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003373:Coumaric Acids / Q000138:chemical synthesis*; D019281:Dimerization; D015195:Drug Design; D004987:Ethers / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011522:Protons; D012701:Serotonin / Q000737:chemistry; D013053:Spectrophotometry / Q000379:methods; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D003373:Coumaric Acids; D004987:Ethers; D026121:Indole Alkaloids; D011522:Protons; D012701:Serotonin