Skip to Content

CN

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

Methanol, suitable for NMR (reference standard)

Sigma-Aldrich

Methanol, purification grade, 99.8%

Sigma-Aldrich

Cesium carbonate, 99.995% trace metals basis

Sigma-Aldrich

Cesium carbonate, 99.9% trace metals basis

Sigma-Aldrich

Cesium carbonate, ReagentPlus^®, 99%

Sigma-Aldrich

Cesium carbonate, 99.95% trace metals basis

Sigma-Aldrich

Cesium carbonate, purum p.a., ≥98.0% (T)

Supelco

Methanol, analytical standard

Sigma-Aldrich

Methanol, anhydrous, 99.8%

Sigma-Aldrich

Cesium carbonate, puriss. p.a., ≥99.0%

Supelco

Methanol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Methanol, suitable for HPLC, ≥99.9%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Methanol, ACS spectrophotometric grade, ≥99.9%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Methanol, puriss., meets analytical specification of Ph Eur, ≥99.7% (GC)

Sigma-Aldrich

Methanol, BioReagent, ≥99.93%

Sigma-Aldrich

Methanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)

Sigma-Aldrich

Methanol, HPLC Plus, ≥99.9%

Sigma-Aldrich

Methanol, suitable for HPLC, gradient grade, ≥99.9%

Sigma-Aldrich

Methanol, suitable for HPLC, gradient grade, suitable as ACS-grade LC reagent, ≥99.9%

Sigma-Aldrich

Methanol, Laboratory Reagent, ≥99.6%

Sigma-Aldrich

Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer

Sigma-Aldrich

N,N-Dimethylacetamide, anhydrous, 99.8%

Sigma-Aldrich

N,N-Dimethylacetamide-d₉, 99 atom % D

Sigma-Aldrich

p-Toluenesulfonyl chloride, reagent grade, ≥98%

Sigma-Aldrich

N,N-Dimethylacetamide, ReagentPlus^®, ≥99%

Sigma-Aldrich

Acetyl chloride solution, 1 M in methylene chloride

Sigma-Aldrich

p-Toluenesulfonyl chloride, ReagentPlus^®, ≥99%