Neil H. Baine

Vinyl radical cyclization in the synthesis of natural products: seychellene

Abstract The use of vinyl radical cyclization in the simplification of synthesis design is probed with the sesquiterpene seychellene as a target. The construction is particularly effective because of very high stereoselectivity in the alkylation of a 2,2,2-bi- cyclo-5-octene-2-one system and because of the control offered by the specific location of the double bond in the product of the vinyl radical cyclization.

An efficient method for the synthesis of substituted TosMIC precursors

Abstract Substituted tosylmethyl isocyanides (TosMICs) are useful reagents for which no general method of preparation is available. We describe here a high-yielding method for the synthesis of substituted tosylmethyl formamides, which are readily converted to the corresponding isocyanides.

Synthesis of 3-carboxy-20-keto steroid, SB 209963, a 5α-reductase inhibitor, by palladium-catalyzed hydroxycarbonylation

Abstract SB 209963 was produced in three steps starting from 17β-carboxyandrost-4-en-3-one. A palladium-catalyzed hydroxycarbonylation introduced the carboxylic acid under mild conditions without epimerization at C-17. This reaction represents the first example of hydroxycarbonylation of a vinyl halide under neutral conditions.