Michael Martin

An exceptionally mild deprotection of phthalimides

Abstract Phthalimides are converted to primary amines in an efficient, two-stage, one-flask operation using NaBH4/2-propanol, then acetic acid.

Epoxides as alkene protecting groups. A mild and efficient deoxygenation

Abstract Dimethyl diazomalonate smoothly deoxygenates epoxides to alkenes with rhodium(II) acetate catalysis.

Synthesis of 2,4-methanoproline

Abstract An efficient synthesis of 2,4-methanoproline from serine is described. The cyclobutane is formed by a sensitized intramolecular [2+2] photoaddition.

Alkylation of the cyclic sulfamate of prolinol. Preparation of optically active 2-alkyl-substituted pyrrolidines

Abstract Treatment of the cyclic sulfamate of (R)-prolinol ( 1 ) with aromatic lithium reagents, followed by acidic hydrolysis, gives 2-substituted pyrrolidines 3a-c in moderate yields.

The synthesis of pacifigorgiol

Pacifigorgiol is a new irregular sesquiterpene isolated from the Pacific gorgonian coral Pacifigoria adamsii. It has modest biological activity as a fish toxin. An 11 step synthesis of racemic pacifigorgiol from commercially available starting material is presented. The ultimately successful route is patterned on a biogenetic speculation. Our current progress toward the synthesis of optically active pacifigorgiol is also described.

Syncarpurea, a novel metabolite from uvaria afzelii

Abstract The isolation and structure determination of syncarpurea (1), a novel urea from Uvaria afzelii is reported.

The synthesis of vafzelin and syncarpin, constitutents of uvaria afzelii

Efficient syntheses of vafzelin and syncarpin, unusual plant metabolites from Uvaria afzelii, are described.