Chan-Hwa Kuo

Total synthesis of the macrolide, zearalenone.

Abstract Total synthesis of the biologically active macrolide zearalenone together with its optical resolution and the determination of its absolute configuration as “S” are described. Wittig condensation with an ortho aldehydic ester proceeded in part with vicinal interaction and formation of an acetylenic product.

A total synthesis of griseofulvin and its optical antipode

Abstract An efficient total synthesis of (+) griseofulvin and its optical antipode, (−) griseofulvin, is described. Several aspects of the chemistry of this substance, its precursors and transformation products are discussed.

A stereoselective total synthesis of (±) prostaglandin E11,2

Abstract A stereoselective total synthesis of prostaglandin E1 employing 5-methoxyindanone-1 as starting material is described.

The synthesis of C3-methyl, C3-decarboxy-zaragozic acid A : a potent squalene synthase inhibitor

Abstract The title compound and its C4-pivaloyloxy methyl (POM) ester have been synthesized by converting zaragozic acid A to the key intermediate of the protected C3-hydroxymethyl compound 6 . Subsequent radical deoxygenation via the Barton-McCombie procedure, followed by deprotection, afforded the product 11 (L-703,370). This compound possesses squalene biosynthesis inhibitory potency of 22% at 24 mpk and its C4-POM ester, 12 (L-735,142), exhibits an ED 50 of 1.6 mpk in our oral mouse assay.