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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

RESUMEN

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.

MATERIALES

Número de producto

Marca

Descripción del producto

Sigma-Aldrich

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

Sigma-Aldrich

ε-Caprolactam, 99%

Sigma-Aldrich

DL-Tartaric acid, ReagentPlus^®, 99%

Sigma-Aldrich

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

Sigma-Aldrich

L-(+)-Tartaric acid, ≥99.5%

Sigma-Aldrich

L-(+)-Tartaric acid, ≥99.7%, FCC, FG

Sigma-Aldrich

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

Sigma-Aldrich

DL-Tartaric acid, ≥99%

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

L-(+)-Tartaric acid, BioXtra

Supelco

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

Sigma-Aldrich

L-(+)-Tartaric acid, JIS special grade, ≥99.5%

Sigma-Aldrich

L-(+)-Tartaric acid, SAJ first grade, ≥99.5%