Publication

First asymmetric synthesis of the cyclohexanone subunit of baconipyrones A and B. Revision of its structure

Pierre Vogel
2004
Journal Articles

Abstract

An asymmetric synthesis of the 3,5-dihydroxycyclohexanone subunit of baconipyrones A and B, as well as that of the hydroxydiketone subunit of baconipyrones C and D ((-)-(4S,6S)-4,6-dimethyl-5-hydroxynonan-3,7-dione), is described. Key steps include sulfur dioxide-induced additions of enoxysilanes to 1,3-dioxy-1,3-dienes, followed by retro-ene desulfitations (retro-ene elimination of SO2).

Official source

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Pierre Vogel
2004
Journal Articles

Abstract

Official source

Related concepts (5)

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.

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.

Persistent data structure

In computing, a persistent data structure or not ephemeral data structure is a data structure that always preserves the previous version of itself when it is modified. Such data structures are effectively immutable, as their operations do not (visibly) update the structure in-place, but instead always yield a new updated structure. The term was introduced in Driscoll, Sarnak, Sleator, and Tarjans' 1986 article. A data structure is partially persistent if all versions can be accessed but only the newest version can be modified.