Polycyclic cembranoids and norcembranoids are a family of highly oxygenated, structurally congested, stereochemically complex diterpenes and norditerpenes. The great synthetic challenges have attracted many attentions from organic community. We envisioned that 1, 3-dipole cycloaddition reaction is highly applicable in constructing the characteristic bowl-shaped polycyclic frameworks in these natural products. Indeed, not only the [6-5-5], but also the [7-5-5] tricyclic framework, could be rapidly assembled in short steps from readily available starting materials. Such a strategy laid solid foundation for solving the synthetic challenges posed by these fascinating molecules. Our progress to the total synthesis of ineleganolide, a representative target in these family will be discussed.

Exploration of intramolecular 1, 3-dipolar cycloaddition reactions for rapid construction of polycyclic cembranoids and norcembranoids

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