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Merck

Enantiospecific total synthesis of (-)-bengamide E.

Chemistry, an Asian journal (2012-12-05)
Prashant K Metri, Raphael Schiess, Kavirayani R Prasad
PMID23208822
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
Referencia del producto
Marca
Descripción del producto
C2204
Sigma-Aldrich
ε-Caprolactam, 99%
251380
Sigma-Aldrich
L-(+)-Tartaric acid, ACS reagent, ≥99.5%
T206
Sigma-Aldrich
D-(−)-Tartaric acid, ReagentPlus®, 99%
T400
Sigma-Aldrich
DL-Tartaric acid, ReagentPlus®, 99%
W304409
Sigma-Aldrich
L-(+)-Tartaric acid, ≥99.7%, FCC, FG
T109
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L-(+)-Tartaric acid, ≥99.5%
W304401
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DL-Tartaric acid, ≥99%
33801
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L-(+)-Tartaric acid, puriss. p.a., reag. ISO, 99.5-101.0% (calc. to the dried substance)
798665
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L-(+)-Tartaric acid, anhydrous, free-flowing, Redi-Dri™, ACS reagent, ≥99.5%
95320
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D-(−)-Tartaric acid, puriss., unnatural form, ≥99.0% (T)
30-0110
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L-(+)-Tartaric acid, JIS special grade, ≥99.5%
T1807
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27506
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L-(+)-Tartaric acid, puriss., meets analytical specification of Ph. Eur., NF, 99.7-100.5% (calc. to the dried substance), powder
41447
Supelco
L-(+)-Tartaric acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
30-0120
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L-(+)-Tartaric acid, SAJ first grade, ≥99.5%