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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%
30-0120
Sigma-Aldrich
L-(+)-Tartaric acid, SAJ first grade, ≥99.5%
30-0110
Sigma-Aldrich
L-(+)-Tartaric acid, JIS special grade, ≥99.5%
95320
Sigma-Aldrich
D-(−)-Tartaric acid, puriss., unnatural form, ≥99.0% (T)
C2204
Sigma-Aldrich
ε-Caprolactam, 99%
33801
Sigma-Aldrich
L-(+)-Tartaric acid, puriss. p.a., reag. ISO, 99.5-101.0% (calc. to the dried substance)
T109
Sigma-Aldrich
L-(+)-Tartaric acid, ≥99.5%
W304409
Sigma-Aldrich
L-(+)-Tartaric acid, ≥99.7%, FCC, FG
T206
Sigma-Aldrich
D-(−)-Tartaric acid, ReagentPlus®, 99%
27506
Sigma-Aldrich
L-(+)-Tartaric acid, puriss., meets analytical specification of Ph. Eur., NF, 99.7-100.5% (calc. to the dried substance), powder
251380
Sigma-Aldrich
L-(+)-Tartaric acid, ACS reagent, ≥99.5%
T1807
Sigma-Aldrich
L-(+)-Tartaric acid, BioXtra
41447
Supelco
L-(+)-Tartaric acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
798665
Sigma-Aldrich
L-(+)-Tartaric acid, anhydrous, free-flowing, Redi-Dri™, ACS reagent, ≥99.5%