C. L. J. Wang

Synthesis and biological properties of 12-fluoroprostacyclins

Abstract The synthesis of the sodium salts of enantiomerically pure 12-fluoroPGI 2 (9), (±)-12-fluoroPGI 2 (9), (±)-15-epi-12-fluoroPGI 2 (10), (±)-12-fluoro-13,14-dihydroPGI 2 (11), (±)-12-fluoro-4(E)-isoPGI 2 (12), and (±)-5,6-dihydro-12-fluoroPGI 2 (13) is detailed starting from the corresponding derivatives of 12-fluoroPGF 2α methyl ester. Prostacyclins 9, (±)-9, (±)-10, (±)-11, (±)-12, and (±)-13 have been evaluated for their ability to inhibit human platelet aggregation and their effect on smooth muscle (isolated cat coronary artery).

Trimethylsilylacetic acid dianion: application to organic synthesis

Trimethylsilylacetic acid readily forms the dianion (2) providing highly efficient routes to α-trimethylsilylcarboxylic acids, α,β-unsaturated acids, and α-trimethylsilyl-γ-butyrolactones; the latter can then be converted into α-ylidene-γ-butyrolactones, α-bromo-γ-butyrolactones and γ-butyrolactones.

Total synthesis of 12-fluoroprostaglandin F2α methyl ester

The total synthesis of 12-fluoroprostaglandin F2α methyl ester (1) from norbornadiene is described which involves the fluorination of the enolate derived from the ester (3) with perchloryl fluoride.

Phenylthioacetic acid dianion: latent vinyl, oxiranyl, and acyl carbanion equivalents

The α-metallated carboxylate salt of phenylthio-acetic acid provides access to a wide variety of β-hydroxy sulphides which are key intermediates for the synthesis of olefins, oxirans, and ketones.

Total synthesis of 12-hydroxymethylprostaglandin F2α methyl ester

The hydroxymethylation of the ester enolate derived from the ester (2) provided the hydroxymethylated adducts (3) and (4) both of which have been successfully converted into 12-hydroxymethylprostaglandin F2α methyl ester(1).