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  • 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

SAFC
N,N-Dimethylacetamide, Ph. Eur.
Supelco
Methylene Chloride, Pharmaceutical Secondary Standard; Certified Reference Material
USP
Methyl alcohol, United States Pharmacopeia (USP) Reference Standard
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Dichloromethane, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains 50-150 ppm amylene as stabilizer
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N,N-Dimethylacetamide, suitable for HPLC, ≥99.9%
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Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer
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Dichloromethane, contains 40-150 ppm amylene as stabilizer, ACS reagent, ≥99.5%
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N,N-Dimethylacetamide, spectrophotometric grade, ≥99%
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Dichloromethane, puriss., meets analytical specification of Ph. Eur., NF, ≥99% (GC)
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Dichloromethane, biotech. grade, 99.9%, contains 40-150 ppm amylene as stabilizer
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N,N-Dimethylacetamide, puriss. p.a., ≥99.5% (GC)
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Acetyl chloride, reagent grade, 98%
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p-Toluenesulfonyl chloride, ReagentPlus®, ≥99%
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N,N-Dimethylacetamide-d9, 99 atom % D
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Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer
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Sodium methoxide solution, 25 wt. % in methanol
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