Publication

Regioselective base-induced ethereal bridge openings of 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic derivatives; Synthesis of squalestatin core analogues

Pierre Vogel
1999
Journal Articles

Abstract

The Diels-Alder adduct of furfuryl alcohol and maleic anhydride was converted into dimethyl 5-exo,6-exo-dihydroxy-1{[tris (isopropyl)silyloxy] methyl} -7-oxabicyclo[2.2.1]heptane-2-exo,3-exo-dicarboxylate (12). Regioselective monosilylation of diol 12 gave the 5-O-(tert-butyl)dimethylsilyl ether 18. Under basic conditions the 7-oxanorbornane system of 18 was isomerized selectively into a 4,5,6-trihydroxy-6-(hydroxymethyl)cyclohex-2-ene-1,2-dicarboxylic derivative that was converted into a doubly-branched hepturonic acid derivative (24), potential precursor for the preparation of squalestatin core analogues.

Official source

https://infoscience.epfl.ch/entities/publication/fbec4ec4-32a5-48b5-b0e7-841d582c8833

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Pierre Vogel
1999
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/fbec4ec4-32a5-48b5-b0e7-841d582c8833

About this result

Related concepts (9)

Organoboron chemistry

Organoboron chemistry or organoborane chemistry is the chemistry of organoboron compounds or organoboranes, which are chemical compounds of boron and carbon that are organic derivatives of borane (BH3), for example trialkyl boranes. . Organoboron compounds are important reagents in organic chemistry enabling many chemical transformations, the most important ones being hydroboration and carboboration. Reactions of organoborates and boranes involve the transfer of a nucleophilic group attached to boron to an electrophilic center either inter- or intramolecularly.

Dicarboxylic acid

In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids. Dicarboxylic acids are used in the preparation of copolymers such as polyamides and polyesters. The most widely used dicarboxylic acid in the industry is adipic acid, which is a precursor in the production of nylon.

Hydroboration

In organic chemistry, hydroboration refers to the addition of a hydrogen-boron bond to certain double and triple bonds involving carbon (, , , and ). This chemical reaction is useful in the organic synthesis of organic compounds. Hydroboration produces organoborane compounds that react with a variety of reagents to produce useful compounds, such as alcohols, amines, or alkyl halides. The most widely known reaction of the organoboranes is oxidation to produce alcohols typically by hydrogen peroxide.