Marco A. Ciufolini

Synthesis of Spirolactams from tyrosine amides and related substances

Abstract Oxidation of oxazolines derived from phenolic ω-arylalkanoic acids such as tyrosine with iodobenzene diacetate leads to spirocyclic amides in moderate yields. This reaction was heretofore unknown due to the propensity of free amide analogs of the oxazolines to furnish lactones upon oxidation.

Efficient palladium-mediated synthesis of a spirocyclic model for fredericamycin A.

Abstract A palladium-promoted intramolecular arylation of a β-diketone generates a spirocyclic system as a model for Fredericamycin A.

Practical total synthesis of (+)-Camptothecin: The full story

Abstract The evolution of our strategy for the synthesis of (+)-Camptothecin and related substances is presented in detail.

A one-step preparation of functionalized 3-cyano-2-pyridones

Abstract Reaction of various enones and enals with cyanoacetamide in DMSO-tBuOK under an oxygen atmosphere furnishes 3-cyanopyridones directly and in good yield.

Reductive cleavage of TROC groups under neutral conditions with cadmium-lead couple

Abstract Cadmium-lead couple induces rapid and efficient reductive cleavage of TROC groups under extremely mild conditions. The couple is readily prepared and it is not pyrophoric.

The aza-achmatowicz rearrangement: A route to useful building blocks for N- containing structures

Abstract N-Acyl 2-furylamines were transformed into 2-alkyl-6-methoxy-hexahydropyridin-3-ones. The rearranged products are useful building blocks for the total synthesis of alkaloids and unusual aminoacids.

Facile palladium-mediated substitution of chlorine in 2-chloroquinolines

Abstract Unlike ordinary aryl chlorides, the title hererocycles participate readily in Castro-Stephens, Stille, Suzuki, and carbonylation reactions under the catalytic influence of Pd(0).

A useful benzannulation reaction

Abstract [(2-Alkynyl)-benzoyl]-acetate esters undergo cycloaromatization in good yield upon treatment with CSA in refluxing chloroform.

Yb(fod)3-promoted ene reaction of aldehydes with vinyl ethers

Abstract Catalytic amounts of Yb(fod) 3 catalyze a bimolecular ene-like reaction between ordinary aldehydes and vinyl ethers, in which the oxygen functionality is located at the central carbon of an allylic system. These reactions proceed at room temperature in high yield.

A PROTECTION SCHEME FOR THE PREPARATION OF ACID CHLORIDES OF SERINE AND THREONINE

Abstract N-acetyl oxazolone derivatives of serine and threonine are readily converted into reactive acid chlorides that condense efficiently with various C-protected aminoacids, even poorly nucleophilic ones.