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Literature DB >> 24916169

Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization.

Abstract

We report a stereodivergent, asymmetric total synthesis of (-)-clusianone in six steps from commercial materials. We implement a challenging cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms. Mechanistic studies point to the unique ability of formic acid to mediate the cyclization forming the clusianone framework.

Entities: Chemical Disease Species

Keywords: PPAPs; cationic cyclization; dearomatization; formic acid; natural products

Mesh：

Substances：

Year: 2014 PMID： 24916169 PMCID： PMC4182949 DOI： 10.1002/anie.201404437

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

44 in total

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8. Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols.

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9. Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone.

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10 in total

1. Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Authors: Mikayo Hayashi; Lauren E Brown; John A Porco
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2. Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-epi-Garcimultiflorone A.

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3. Syntheses of (+)-30-epi-, (-)-6-epi-, (±)-6,30-epi-13,14-Didehydroxyisogarcinol and (±)-6,30-epi-Garcimultiflorone A Utilizing Highly Diastereoselective, Lewis Acid-Controlled Cyclizations.

Authors: Jonathan H Boyce; Vincent Eschenbrenner-Lux; John A Porco
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4. Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

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Journal: Angew Chem Int Ed Engl Date: 2019-09-25 Impact factor: 15.336

Review 5. An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

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6. Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.

Authors: Alexander J Grenning; Jonathan H Boyce; John A Porco
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7. 7-epi-Clusianone, a Multi-Targeting Natural Product with Potential Chemotherapeutic, Immune-Modulating, and Anti-Angiogenic Properties.

Authors: Wesley F Taylor; Maria Yanez; Sara E Moghadam; Mahdi Moridi Farimani; Sara Soroury; Samad N Ebrahimi; Marzieh Tabefam; Ehsan Jabbarzadeh
Journal: Molecules Date: 2019-12-03 Impact factor: 4.411