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Enantiospecific total synthesis of (-)-bengamide E.

Enantiospecific total synthesis of (-)-bengamide E.

Chemistry, an Asian journal (2012-12-05)

Prashant K Metri, Raphael Schiess, Kavirayani R Prasad

ZUSAMMENFASSUNG

Total synthesis of the polyhydroxy caprolactam amide natural product, bengamide E, is accomplished starting from tartaric acid. Key reactions in the synthesis include desymmetrization of the bis(dimethylamide) unit of tartaric acid, Zn(BH(4))(2)-mediated anti-selective reduction, and a Horner-Wadsworth-Emmons olefination.

MATERIALIEN

Produktnummer

Marke

Produktbeschreibung

Sigma-Aldrich

ε-Caprolactam, 99%

Sigma-Aldrich

D-(−)-Weinsäure, ReagentPlus^®, 99%

Sigma-Aldrich

DL-Tartarsäure, ReagentPlus^®, 99%

Sigma-Aldrich

L-(+)-Tartarsäure, ≥99.7%, FCC, FG

Sigma-Aldrich

L-(+)-Tartarsäure, ACS reagent, ≥99.5%

Sigma-Aldrich

DL-Tartarsäure, ≥99%

Sigma-Aldrich

L-(+)-Tartarsäure, ≥99.5%

Sigma-Aldrich

L-(+)-Tartarsäure, anhydrous, free-flowing, Redi-Dri^™, ACS reagent, ≥99.5%

Sigma-Aldrich

L-(+)-Tartarsäure, puriss. p.a., reag. ISO, 99.5-101.0% (calc. to the dried substance)

Sigma-Aldrich

D-(−)-Weinsäure, puriss., unnatural form, ≥99.0% (T)

Sigma-Aldrich

L-(+)-Tartarsäure, BioXtra

Sigma-Aldrich

L-(+)-Tartarsäure, puriss., meets analytical specification of Ph. Eur., NF, 99.7-100.5% (calc. to the dried substance), powder

Supelco

L-(+)-Tartarsäure, certified reference material, TraceCERT^®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland