Merck
  • Home
  • Search Results
  • Total synthesis of putative montamine and a proposed structural reassignment.

Total synthesis of putative montamine and a proposed structural reassignment.

Organic & biomolecular chemistry (2014-07-24)
Lachlan M Blair, Elizabeth A Colby Davie, Jonathan Sperry
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium hydride, 60 % dispersion in mineral oil
Sigma-Aldrich
Methanol, anhydrous, 99.8%
Supelco
Methanol, analytical standard
Sigma-Aldrich
Cesium carbonate, puriss. p.a., ≥99.0%
Sigma-Aldrich
Cesium carbonate, purum p.a., ≥98.0% (T)
Supelco
Methanol, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Cesium carbonate, 99.95% trace metals basis
Sigma-Aldrich
Cesium carbonate, 99.995% trace metals basis
Sigma-Aldrich
Cesium carbonate, ReagentPlus®, 99%
Sigma-Aldrich
Cesium carbonate, 99.9% trace metals basis
Sigma-Aldrich
Sodium hydride, dry, 90%
Sigma-Aldrich
Methanol, NMR reference standard
Sigma-Aldrich
Methanol, Laboratory Reagent, ≥99.6%
Sigma-Aldrich
Methanol, Absolute - Acetone free
Sigma-Aldrich
Methanol, ACS reagent, ≥99.8%
Sigma-Aldrich
Methanol, BioReagent, ≥99.93%
Sigma-Aldrich
Methanol, puriss., meets analytical specification of Ph Eur, ≥99.7% (GC)
Sigma-Aldrich
Methanol, ACS spectrophotometric grade, ≥99.9%
Sigma-Aldrich
Methanol, suitable for HPLC, ≥99.9%
Sigma-Aldrich
Methanol, suitable for HPLC, gradient grade, ≥99.9%
Sigma-Aldrich
Methanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)
Sigma-Aldrich
Methanol, ACS reagent, ≥99.8%
Sigma-Aldrich
Methanol, suitable for HPLC, gradient grade, suitable as ACS-grade LC reagent, ≥99.9%
Sigma-Aldrich
p-Toluenesulfonyl chloride, reagent grade, ≥98%
Sigma-Aldrich
N,N-Dimethylacetamide, ReagentPlus®, ≥99%
Sigma-Aldrich
N,N-Dimethylacetamide-d9, 99 atom % D
Sigma-Aldrich
Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer
Sigma-Aldrich
Sodium methoxide solution, ACS reagent, 0.5 M CH3ONa in methanol (0.5N)
Sigma-Aldrich
Sodium methoxide solution, 25 wt. % in methanol
Sigma-Aldrich
Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer