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ChemInform Abstract: Carbocyclic Ring Construction via an Intramolecular Diels—Alder Reaction of an in situ-Generated, Heteroatom-Stabilized Allyl Cation: Total Synthesis of (.+-.)-Lycopodine.

✍ Scribed by P. A. GRIECO; Y. DAI

Publisher: John Wiley and Sons
Year: 2010
Weight: 38 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199837214

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✦ Synopsis

Carbocyclic Ring Construction via an Intramolecular Diels-Alder Reaction of an in situ-Generated, Heteroatom-Stabilized Allyl Cation: Total Synthesis of (±)-Lycopodine.

-The title compound (X) is totally synthesized using a [4 + 2] cycloaddition leading to the tricyclic compound (VI) possessing all the necessary C atoms needed for the elaboration of (X), radical cyclization leading to the exclusive formation of (VIII) containing the correct stereocenter at C-15, and a Stieglitz rearrangement to establish the bridgehead N atom as the key steps. -(GRIECO,

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ChemInform Abstract: Functionalized Carb

ChemInform Abstract: Functionalized Carbocyclic Rings via Intramolecular Diels—Alder Reactions of in situ Generated, γ Substituted, Heteroatom-Stabilized Allyl Cations in Acidic Polar Media.

✍ Paul A. Grieco; Michael D. Kaufman 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB

Functionalized Carbocyclic Rings via Intramolecular Diels-Alder Reactions of in situ Generated, γ Substituted, Heteroatom-Stabilized Allyl Cations in Acidic Polar Media. -Slow addition of substrates such as (I) and (III) to a solution of lithium perchlorate and catalytic TFA generates oxygen stabil