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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
PMID23208822
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
W304401
Sigma-Aldrich
DL-Tartaric acid, ≥99%
T400
Sigma-Aldrich
DL-Tartaric acid, ReagentPlus®, 99%
41447
Supelco
L-(+)-Tartaric acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
95320
Sigma-Aldrich
D-(−)-Tartaric acid, puriss., unnatural form, ≥99.0% (T)
W304409
Sigma-Aldrich
L-(+)-Tartaric acid, ≥99.7%, FCC, FG
T206
Sigma-Aldrich
D-(−)-Tartaric acid, ReagentPlus®, 99%
T109
Sigma-Aldrich
L-(+)-Tartaric acid, ≥99.5%
251380
Sigma-Aldrich
L-(+)-Tartaric acid, ACS reagent, ≥99.5%
33801
Sigma-Aldrich
L-(+)-Tartaric acid, puriss. p.a., reag. ISO, 99.5-101.0% (calc. to the dried substance)
C2204
Sigma-Aldrich
ε-Caprolactam, 99%
T1807
Sigma-Aldrich
L-(+)-Tartaric acid, BioXtra
27506
Sigma-Aldrich
L-(+)-Tartaric acid, puriss., meets analytical specification of Ph. Eur., NF, 99.7-100.5% (calc. to the dried substance), powder
798665
Sigma-Aldrich
L-(+)-Tartaric acid, anhydrous, free-flowing, Redi-Dri™, ACS reagent, ≥99.5%