Publication

Total asymmetric synthesis of seco-acids of 9,12-anhydroerythronolide aglycons

Pierre Vogel
1998
Journal Articles

Abstract

The Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'S)-camphanate was converted into (2R,3R,4S,5S,6R,7R)-3,6-epoxy-4,5-isopropylidenedioxy-2,4,6-trimethyl-7- [(tert-butyl)-dimethylsilyloxy]non-1-yl phenyl sulfoxides (6), the condensation of which with (3R,4S,5R,6S)-7-benzyloxy-3,5-isopropylidenedioxy-4,6-dimethylheptan-2-o ne (7) led to the partially-protected seco-acid of the 9,12-anhydroerythronolide aglycon (5). (C) 1998 Elsevier Science Ltd. All rights reserved.

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Pierre Vogel
1998
Journal Articles

Abstract

Official source

Related concepts (6)

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.

Sulfoxide

In organic chemistry, a sulfoxide, also called a sulfoxide, is an organosulfur compound containing a sulfinyl () functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent. Sulfoxides feature relatively short S–O distances. In DMSO, the S–O distance is 1.531 Å.

Asymmetric induction

Asymmetric induction (also enantioinduction) describes the preferential formation in a chemical reaction of one enantiomer or diastereoisomer over the other as a result of the influence of a chiral feature present in the substrate, reagent, catalyst or environment. Asymmetric induction is a key element in asymmetric synthesis. Asymmetric induction was introduced by Hermann Emil Fischer based on his work on carbohydrates. Several types of induction exist.

Related publications (1)

Total asymmetric synthesis of seco-acids of 9,12-anhydroerythronolide aglycons

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Total, asymmetric synthesis of ethyl D-ido-4-heptulosuronate derivatives starting from diethyl 4-oxopimelate