Studies toward the Tricyclic Core of Phomactin A. Synthesis of the Reduced Furanochroman Subunit

An approach to the tricyclic core of phomactin A is described via the synthesis of a reduced furanochroman model. Key elements of this study include the use of a highly functionalized 1-oxadecalone derivative as a template for the stereoselective introduction of functionality and a tandem retro aldol−epoxide opening−cyclization sequence for elaboration of the dihydrofuran ring

On the Stereochemistry of the Dihydropyrone Diels−Alder Reaction

The Diels−Alder reaction of activated dihydropyrones with electron-rich dienes proceeds with synthetically useful levels of diastereoselectivity. Product ratios vary with the nature and location of substituents on diene and dienophile, as well as with reaction conditions. Lewis acid catalyzed reactions of related pyrone and benzopyrone dienophiles are also diastereoselective

Synthesis of 1-Oxadecalones via the Lewis Acid Catalyzed Dihydropyrone Diels−Alder Reaction

Synthesis of 1-Oxadecalones via the Lewis Acid Catalyzed Dihydropyrone Diels−Alder Reactio

Dihydropyrones as Dienophiles in the Diels−Alder Reaction: Application to the Synthesis of 1-Oxadecalones

Dihydropyrones as Dienophiles in the Diels−Alder Reaction:  Application to the Synthesis of 1-Oxadecalone

2‑Methylenetetrahydropyrans: Efficient Partners in the Carbonyl Ene Reaction

The carbonyl ene reaction of 2-methylenetetrahydropyrans provides a rapid, high yielding route for the preparation of β-hydroxydihydropyrans under mild conditions. This process provides a new entry for the synthesis of 2-substituted tetrahydropyrans and for the direct introduction of oxygen heterocycles into molecular frameworks