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Enantiospecific Total Synthesis of Natural (+)-Taxusin. 1. Retrosynthesis, Advancement to Diastereomeric trans-Δ9,10-Tricyclic Olefinic Intermediates, and the Stereocontrol Attainable Because of
In a study directed toward the expeditious construction of heavily functionalized taxane intermediates, 1-vinyl-2-cyclohexenyl-7,7-dimethyl-exo-norbornan-2-ols such as 9, which are derived from
A Convenient Method for Determining the Concentration of Grignard Reagents
Abstract A convenient procedure for the quantitative assay of alkyl, aryl, and vinyl Grignard reagent concentrations is described. Through the combined use of menthol and 1,10-phenanthroline in dry
The α‐Hydroxy Ketone (α‐Ketol) and Related Rearrangements †
Treatment of suitable alpha-hydroxy aldehydes and ketones with a base, a Bronsted or Lewis acid, or simply with heat has long been know to induce the 1,2-shift of an alkyl or aryl substituent to form
Convergent enantioselective synthesis of vinigrol, an architecturally novel diterpenoid with potent platelet aggregation inhibitory and antihypertensive properties. 1. Application of anionic
The coupling of building blocks 15 and 36e in the presence of MgBr(2).OEt(2) at 0 degrees C proceeds with an exo stereoselectivity (3.2:1) considerably more advantageous for the acquisition of
Stereoselective synthesis of beta-anomeric 4'-thiaspirocyclic ribonucleosides carrying the full complement of RNA-level hydroxyl substitution.
Although differences in reactivity between the two stereoisomeric series were noted, the common route has successfully given rise for the first time to desirable beta-anomeric sulfur-containing spiroribonucleosides with minimum formation of the alpha-anomers.
Teubrevin G and teubrevin H: the first total syntheses of rearranged neo-clerodanes including solutions to the problems of chirality merger and furan ring assembly.
The reported strategy relies on a highly regioselective cycloaddition-fragmentation approach to the construction of a 2,3,4-trisubstituted furan and features efficient ring-closing metathesis chemistry made possible through the application of a 1,3-dimesityl-4,5-dihydroimidazol-2-ylideneruthenium precatalyst.