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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

RÉSUMÉ

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.

MATÉRIAUX

Référence du produit

Marque

Description du produit

Sigma-Aldrich

ε-Caprolactam, 99%

Sigma-Aldrich

L-(+)-Tartaric acid, ACS reagent, ≥99.5%

Sigma-Aldrich

D-(−)-Tartaric acid, ReagentPlus^®, 99%

Sigma-Aldrich

DL-Tartaric acid, ReagentPlus^®, 99%

Sigma-Aldrich

L-(+)-Tartaric acid, ≥99.7%, FCC, FG

Sigma-Aldrich

L-(+)-Tartaric acid, ≥99.5%

Sigma-Aldrich

DL-Tartaric acid, ≥99%

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

L-(+)-Tartaric acid, BioXtra

Sigma-Aldrich

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

Supelco

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