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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
L-(+)-Tartaric acid, JIS special grade, ≥99.5%
Sigma-Aldrich
L-(+)-Tartaric acid, SAJ first grade, ≥99.5%
Supelco
L-(+)-Tartaric acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
D-(−)-Tartaric acid, puriss., unnatural form, ≥99.0% (T)
Sigma-Aldrich
L-(+)-Tartaric acid, ≥99.7%, FCC, FG
Sigma-Aldrich
D-(−)-Tartaric acid, ReagentPlus®, 99%
Sigma-Aldrich
L-(+)-Tartaric acid, ≥99.5%
Sigma-Aldrich
L-(+)-Tartaric acid, ACS reagent, ≥99.5%
Sigma-Aldrich
L-(+)-Tartaric acid, puriss. p.a., reag. ISO, 99.5-101.0% (calc. to the dried substance)
Sigma-Aldrich
ε-Caprolactam, 99%
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
Sigma-Aldrich
L-(+)-Tartaric acid, anhydrous, free-flowing, Redi-Dri, ACS reagent, ≥99.5%