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

ARK2190

SAFC

N,N-Dimethylacetamide, Ph. Eur.

PHR1557

Supelco

Methylene Chloride, Pharmaceutical Secondary Standard; Certified Reference Material

1424109

USP

Methyl alcohol, United States Pharmacopeia (USP) Reference Standard

34856

Sigma-Aldrich

Dichloromethane, suitable for HPLC, ≥99.8%, contains amylene as stabilizer

650463

Sigma-Aldrich

Dichloromethane, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains 50-150 ppm amylene as stabilizer

270555

Sigma-Aldrich

N,N-Dimethylacetamide, suitable for HPLC, ≥99.9%

676853

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

D137510

Sigma-Aldrich

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

D65100

Sigma-Aldrich

Dichloromethane, contains 40-150 ppm amylene as stabilizer, ACS reagent, ≥99.5%

154806

Sigma-Aldrich

N,N-Dimethylacetamide, spectrophotometric grade, ≥99%

24233

Sigma-Aldrich

Dichloromethane, puriss., meets analytical specification of Ph. Eur., NF, ≥99% (GC)

494453

Sigma-Aldrich

Dichloromethane, biotech. grade, 99.9%, contains 40-150 ppm amylene as stabilizer

38840

Sigma-Aldrich

N,N-Dimethylacetamide, puriss. p.a., ≥99.5% (GC)

320269

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

32222

Sigma-Aldrich

Dichloromethane, puriss. p.a., ACS reagent, reag. ISO, ≥99.9% (GC)

708496

Sigma-Aldrich

Acetyl chloride solution, 1 M in methylene chloride

723851

Supelco

Dichloromethane solution, contains 10 % (v/v) methanol

T35955

Sigma-Aldrich

p-Toluenesulfonyl chloride, reagent grade, ≥98%

185884

Sigma-Aldrich

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

114189

Sigma-Aldrich

Acetyl chloride, reagent grade, 98%

240877

Sigma-Aldrich

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

164992

Sigma-Aldrich

Sodium methoxide, reagent grade, 95%, powder

270997

Sigma-Aldrich

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

271012

Sigma-Aldrich

N,N-Dimethylacetamide, anhydrous, 99.8%

522414

Sigma-Aldrich

N,N-Dimethylacetamide-d₉, 99 atom % D

439223

Sigma-Aldrich

Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer

156256

Sigma-Aldrich

Sodium methoxide solution, 25 wt. % in methanol

00990

Sigma-Aldrich

Acetyl chloride, puriss. p.a., ≥99.0% (T)

17308

Sigma-Aldrich

N,N-Dimethylacetamide, suitable for peptide synthesis, ≥99.8% (GC)

02575

Supelco

Dichloromethane, analytical standard