Norma K. Dunlap

Cuprate additions to 5-methoxycyclopentenones: a novel stereoelectronic effect

Abstract Cuprate additions to 5-methoxy-2-cyclopentenone have been found to proceed with moderate to extremely high diastereofacial selectivity, depending upon the specific cuprate and reaction protocol employed. Comparisons with related 5-substituted cyclopentenones suggest that the observed selectivity is not simply steric in nature, but instead reflects a novel stereoelectronic effect.

Total synthesis of dechloromikrolin: A structural reassignment with biosynthetic implications

Abstract The total synthesis of dechloromikrolin ( 2Z ), a minor fungal metabolite derived from Gilmaniella humicola Barron, has been achieved. The synthesis resulted in a reassignment of the stereochemistry of the C(2, 3)-disubstituted olefinic bond from E to Z . The biosynthetic implications of this reassignment are discussed.

Total synthesis of (+)-mikrolin

Abstract The total synthesis of (+)-mikrolin ( 1a ), a novel fungal metabolite derived from Gilmaniella humicola Barron, has been achieved. The key step entailed a stereoselective hydroxyldirected cis -hydrogenation to set the requisite stereogenic center at C(9).

Concise Synthesis of Enantiomers of 4-Aminobutane-1,2,3-triol

A very efficient synthesis of (2R,3S) and (2S,3R)-4-aminobutane-1,2,3-triol has been developed using either d- or l-glucose as the starting material. A key step is the one-pot conversion of an aldehyde to an amide, the scope of which has been extended to include other carbohydrate-derived aldehydes.