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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

ABSTRACT

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.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

DL-Tartaric acid, ≥99%

Sigma-Aldrich

DL-Tartaric acid, ReagentPlus^®, 99%

Sigma-Aldrich

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

Sigma-Aldrich

ε-Caprolactam, 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, ≥99.5%

Sigma-Aldrich

L-(+)-Tartaric acid, ≥99.7%, FCC, FG

Sigma-Aldrich

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

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

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

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, anhydrous, free-flowing, Redi-Dri^™, ACS reagent, ≥99.5%